Herbicidal orthosulfonamide benzene sulfonylureas

ABSTRACT

Ortho-Sulfonamide benzenesulfonylureas, such as N-cyclopropyl-N&#39;-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benz enedisulfonamide, are useful as pre-emergent and post-emergent herbicides.

This is a divisional application of application Ser. No. 810,336, filedon Dec. 23, 1985, now U.S. Pat. No. 4,802,906 which is acontinuation-in-part of application Ser. No. 703,669, filed on Feb. 21,1985, now abandoned.

BACKGROUND OF THE INVENTION

Certain ortho-aminosulfonyl benzenesulfonylureas are known asherbicides. U.S. Pat. No. 4,310,346 discloses, in part, herbicidalsulfonamides of formula ##STR1## wherein: R₂ is H, C₁ to C₆ alkyl, C₃ toC₄ alkenyl, C₃ to C₆ cycloalkyl, C₄ to C₇ cycloalkylalkyl, C₅ to C₆cycloalkenyl, C₃ to C₅ alkynyl, C₃ to C₆ cycloalkyl substituted with 1-2CH₃ groups, CF₂ CF₂ H, CF₂ CHFCl, CF₂ CHFBr, CF₂ CHFCF₃, C(CH₃)₂ CN,(CH₂)_(m) CN, where m is 1 or 2, CH₂ CH₂ OCH₃, CH₂ CH(CH₃)OCH₃, (CH₂)₃OCH₃, CHR₇ CO₂ R₈ or CHR₇ CON(R₈)₂ ; and

R₃ is C₁ to C₄ alkyl, C₃ to C₄ alkenyl, CH₂ CH₂ OCH₃, CH₂ CH(CH)₃ OCH₃,CH₂ CF₃ or (CH₂)_(m) CN, where m is 1 or 2 or CHR₇ CO₂ R₈.

U.S. Pat. No. 4,478,635 discloses, in part, herbicidal sulfonamides offormula ##STR2## wherein: R₁₄ is H, OCH₃, OC₂ H₅, C₁ to C₄ alkyl or CO₂R₁₂ ; and

R₁₅ is H or C₁ to C₄ alkyl.

EPA No. 84305305.9 discloses, in part, herbicidal sulfonylureas offormula ##STR3## wherein: Q is NR₁ R₂, ##STR4## R₁ is H, C(O)R₃, C(O)NR₄R₅, CO₂ R₆, C(O)NHR₉ or CF₂ H; and

R₂ is H or C₁ to C₃ alkyl.

U.S. Pat. No. 4,339,267 discloses, in part, herbicidal sulfonamides offormula ##STR5## wherein: R₁ is ##STR6## R₂ is, among others, SO₂ NR₁₀R₁₁ or SO₂ N(OCH₃)CH₃ ; and

R₁₀ and R₁₁ are independently C₁ to C₆ alkyl or C₃ to C₄ alkenyl or R₁₀and R₁₁ can be taken together to be (CH₂)₄, (CH₂)₅ or O(CH₂ CH₂)₂.

U.S. Pat. No. 4,496,392 discloses, in part, herbicidal sulfonamides offormula ##STR7## wherein: R₁ is, among others, SO₂ NR₈ R₉ or SO₂N(CH₃)OCH₃ ;

R₈ is CH₃ ; and

R₉ is C₁ to C₃ alkyl.

U.S. Pat. No. 4,487,626 discloses, in part, herbicidal sulfonamides offormula ##STR8## wherein: R is, among others, SO₂ NR⁶ R⁷ or SO₂N(OCH₃)CH₃ ; and

R⁶ and R⁷ are independently C₁ to C₄ alkyl, provided that the totalnumber of carbon atoms of R⁶ and R⁷ is less than or equal to 5.

Japanese Patent Application No. 60-166668 (laid open 8/29/85) disclosesherbicidal sulfonamides of the formula ##STR9## wherein: R¹, R² and R³are lower alkyl.

SUMMARY OF THE INVENTION

This invention pertains to compounds of Formula I, agriculturallysuitable compositions containing them and their method-of-use as generaland/or selective preemergent and/or postemergent herbicides or plantgrowth regulants. The compounds are: ##STR10## and their agriculturallysuitable salts, wherein: ##STR11## W is O or S; R is H or CH₃ ;

R₁ is H, C₁ to C₃ alkyl, C₁ to C₃ haloalkyl, halogen, nitro, C₁ to C₃alkoxy, SO₂ NR_(a) R_(b), C₁ to C₃ alkylthio, C₁ to C₃ alkylsulfinyl, C₁to C₃ alkylsulfonyl, CN, CO₂ R_(c), C₁ to C₃ haloalkoxy, C₁ to C₃haloalkylthio, C₂ to C₃ alkoxyalkyl, C₂ to C₃ haloalkoxyalkyl, C₂ to C₃alkylthioalkyl, C₂ to C₃ haloalkylthioalkyl, C₂ to C₃ cyanoalkyl orNR_(d) R_(e) ;

R_(a) is H, C₁ to C₄ alkyl, C₂ to C₃ cyanoalkyl, methoxy or ethoxy;

R_(b) is H, C₁ to C₄ alkyl or C₃ to C₄ alkenyl; or

R_(a) and R_(b) can be taken together as --(CH₂)₃ --, --(CH₂)₄ --,--(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ --;

R_(c) is C₁ to C₄ alkyl, C₃ to C₄ alkenyl, C₃ to C₄ alkynyl, C₂ to C₄haloalkyl, C₂ to C₃ cyanoalkyl, C₅ to C₆ cycloalkyl, C₄ to C₇cycloalkylalkyl or C₂ to C₄ alkoxyalkyl;

R_(d) and R_(e) are independently H or C₁ to C₂ alkyl;

R₂ is C₅ to C₆ alkyl, C₅ to C₆ alkenyl, C₂ to C₆ haloalkenyl, C₃ to C₆alkynyl, C₃ to C₆ cycloalkyl, C₃ to C₆ cycloalkyl optionally substitutedwith 1 or 2 CH₃ groups, C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl,C₃ to C₆ epoxyalkyl, C₂ to C₆ haloalkyl, CH₂ CH(OR₅)₂, ##STR12## (CH₂)₃OCH₃, phenyl which may be optionally substituted with R₇, ##STR13## CH₂C(O)CH₃, CN, OR₆, C₁ to C₆ alkyl substituted with OR₉, S(O)_(n) R₁₀ orNR₁₁ R₁₂, Q, CHR₈ Q or CH₂ CH₂ Q;

R₃ is C₁ to C₆ alkyl, C₃ to C₆ alkenyl, C₃ to C₆ alkynyl, C₃ to C₆cycloalkyl which can be optionally substituted with 1 or 2 CH₃ groups,C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl, C₁ to C₆ haloalkyl, C₁to C₅ alkoxy, C₃ to C₆ epoxyalkyl or C₁ to C₆ alkyl substituted withOR₉, S(O)_(n) R₁₀, NR₁₁ R₁₂ or P(O)(OR₅)₂ ;

R₄ is C₁ to C₃ alkyl substituted with 1-3 atoms of F, Cl or Br, C₃ to C₄alkynyl, CH₂ CH(OR₅)₂, ##STR14## C₂ to C₆ haloalkenyl, C₃ to C₆epoxyalkyl, CH₂ C(O)CH₃, CN, C₁ to C₆ alkyl substituted with OR₉,S(O)_(n) R₁₀ or NR₁₁ R₁₂, Q, CHR₈ Q or CH₂ CH₂ Q;

R₃ and R₄ can be taken together with the sulfonamide nitrogen to form asaturated 5- or 6-membered ring substituted by one or more groupsselected from L or a partially saturated 5- or 6-membered ringoptionally substituted by one or more groups selected from L;

R₅ is C₁ to C₃ alkyl;

R₆ is C₁ to C₅ alkyl;

R₇ is H, C₁ to C₃ alkyl, halogen, NO₂, CF₃, CN or C₁ to C₃ alkoxy;

R₈ is H or CH₃ ;

R₉ is H, SO₂ R₅, C(O)R₅, CO₂ R₅, C(O)NR₁₁ R₁₂ or P(O)(OR₅)₂ ;

R₁₀ is C₁ to C₃ alkyl;

R₁₁ is H or C₁ to C₃ alkyl;

R₁₂ is H or C₁ to C₃ alkyl;

m is 2 or 3;

n is 0, 1 or 2;

Q is a saturated 5- or 6-membered ring which is bonded through a carbonatom and contains 1 heteroatom selected from oxygen, sulfur, or nitrogenor an unsaturated or partially unsaturated 5- or 6-membered ring whichis bonded through a carbon atom and contains 1 to 3 hetero atomsselected from 1 sulfur, 1 oxygen or 1 to 3 nitrogen; and Q can beoptionally substituted by one or more groups selected from L;

L is C₁ to C₄ alkyl, C₁ to C₃ haloalkyl, halogen, C₁ to C₃ alkoxy, C₁ toC₃ alkylthio, C₃ to C₄ alkenyloxy, C₃ to C₄ alkenylthio, C₁ to C₂haloalkoxy or C₁ to C₂ haloalkylthio;

A is ##STR15## X is H, C₁ to C₄ alkyl, C₁ to C₄ alkoxy, C₁ to C₄haloalkoxy, C₁ to C₄ haloalkyl, C₁ to C₄ haloalkylthio, C₁ to C₄alkylthio, halogen, C₂ to C₅ alkoxyalkyl, C₂ to C₅ alkoxyalkoxy, amino,C₁ to C₃ alkylamino or di(C₁ to C₃ alkyl)amino;

Y is H, C₁ to C₄ alkyl, C₁ to C₄ alkoxy, C₁ to C₄ haloalkoxy, C₁ to C₄haloalkylthio, C₁ to C₄ alkylthio, C₂ to C₅ alkoxyalkyl, C₂ to C₅alkoxyalkoxy, amino, C₁ to C₃ alkylamino, di(C₁ to C₃ alkyl)amino, C₃ toC₄ alkenyloxy, C₃ to C₄ alkynyloxy, C₂ to C₅ alkylthioalkyl, C₁ to C₄haloalkyl, C₃ to C₅ cycloalkyl, C₂ to C₄ alkynyl, C(O)R_(f), ##STR16##or N(OCH₃)CH₃ ; L₁ and L₂ are independently O or S;

R_(f) is H or CH₃ ;

R_(g) and R_(h) are independently C₁ to C₂ alkyl;

Z is CH or N;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H;

Y₂ is H or CH₃ ;

X₂ is CH₃ or OCH₃ ;

provided that:

(a) when X is Cl, F, Br or I, then Z is CH and Y is OCH₃, OC₂ H₅,N(OCH₃)CH₃, NHCH₃ or N(CH₃)₂ ;

(b) when R₂ is CH₂ CF₃ and A is A-1 then one or both of X and Y is OCF₂H;

(c) when R₃ or R₄ is CH₂ CF₃, then the other is CHF₂, CH₂ CH₂ F, CH₂ CH₂Cl, CH₂ CH₂ Br or CH₂ CF₃ ;

(d) when R₄ is CF₂ H, then R₃ is other than C₁ to C₃ alkyl;

(e) when R₄ is C₃ to C₄ alkynyl, then R₃ is CHF₂, CH₂ CH₂ F, CH₂ CH₂ Cl,CH₂ CH₂ Br or C₃ to C₄ alkynyl;

(f) when one or both of X and Y is OCF₂ H, then R₆ is C₃ to C₅ alkyl;

(g) when R₂ is OR₆ and A is A-1 wherein Z is CH, then one or both of Xand Y is other than C₁ to C₄ alkyl; and

(h) when X or Y is OCF₂ H, then Z is CH.

In the preceding definitions, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or thedifferent butyl, pentyl and hexyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the differentbutoxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g., vinyl,1-propenyl, 2-propenyl, 3-propenyl and the different butenyl, pentyl andhexenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl,1-propynyl, 2-propynyl and the different butynyl, pentyl and hexynylisomers.

Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

C₄ to C₇ cycloalkylalkyl means cyclopropylmethyl throughcyclopropylbutyl or cyclohexylmethyl.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl" said alkyl may bemonohalogenated or fully substituted with halogen atoms, which may bethe same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃and CH₂ CHFCl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) to C_(j) prefix where i and j are numbers from 1 to 7. Forexample, C₁ to C₃ alkylsulfonyl would designate methylsulfonyl throughpropylsulfonyl, C₂ alkoxyalkoxy would designate OCH₂ OCH₃ ; C₄alkoxyalkoxy would designate the various isomers of an alkoxy groupsubstituted with a second alkoxy group containing a total of 4 carbonatoms, examples including OCH₂ OCH₂ CH₂ CH₃ and OCH₂ CH₂ OCH₂ CH₃ ; as afurther example, C₂ cyanoalkyl would designate CH₂ CN and C₃ cyanoalkylwould designate CH₂ CH₂ CN and CH(CN)CH₃.

Preferred compounds for reasons of increased ease of synthesis and/orgreater herbicidal efficacy are:

(1) Compounds of Formula I wherein:

W is O;

J is J-1; and

R₂ is C₅ to C₆ alkyl, C₅ to C₆ alkenyl, C₂ to C₆ haloalkenyl, C₃ to C₆alkynyl, C₃ to C₆ cycloalkyl, C₃ to C₆ cycloalkyl optionally substitutedwith 1 or 2 CH₃ groups, C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl,C₃ to C₆ epoxyalkyl, C₂ to C₆ haloalkyl, CH₂ CH(OR₅)₂, (CH₂)₃ OCH₃, OR₆,phenyl which can be optionally substituted with R₇, ##STR17## CH₂C(O)CH₃, CN or C₁ to C₆ alkyl substituted with OR₉, S(O)_(n) R₁₀ or NR₁₁R₁₂.

(2) Compounds of Formula I wherein:

W is O;

J is J-1; and

R₂ is Q, CHR₈ Q or CH₂ CH₂ Q.

(3) Compounds of Formula I wherein:

W is O;

J is J-2.

More preferred compounds (4) include those of (1) wherein:

R is H;

R₁ is H, C₁ to C₂ alkyl, F, Cl, Br, NO₂, C₁ to C₂ alkoxy, C₁ to C₂alkylthio, C₁ to C₂ haloalkoxy, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN and is notpara to the sulfonylurea bridge;

A is A-1;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, I, CH₂ F, OCF₂ H, OCH₂ CH₂ F, OCH₂CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ to C₃ alkyl, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃,N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂OCH₃, CH₂ SCH₃, SCF₂ H, cyclopropyl, C.tbd.CH, C.tbd.CCH₃ or CH(OCH₃)₂.

More preferred compounds (5) include those of (2) wherein:

R is H;

R₁ is H, C₁ to C₂ alkyl, F, Cl, Br, NO₂, C₁ to C₂ alkoxy, C₁ to C₂alkylthio, C₁ to C₂ haloalkoxy, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN and is notpara to the sulfonylurea bridge;

A is A-1;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, I, CH₂ F, OCF₂ H, OCH₂ CH₂ F, OCH₂CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ to C₃ alkyl, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃,N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂OCH₃, CH₂ SCH₃, SCF₂ H, cyclopropyl, C.tbd.CH, C.tbd.CCH₃ or CH(OCH₃)₂.

More preferred compounds (6) include those of (3) wherein:

R is H;

R₁ is H, C₁ to C₂ alkyl, F, Cl, Br, NO₂, C₁ to C₂ alkoxy, C₁ to C₂alkylthio, C₁ to C₂ haloalkoxy, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN and is notpara to the sulfonylurea bridge;

A is A-1;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, I, CH₂ F, OCF₂ H, OCH₂ CH₂ F, OCH₂CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br; and

Y is H, C₁ to C₃ alkyl, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃,N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂OCH₃, CH₂ SCH₃, SCF₂ H, cyclopropyl, C.tbd.CH, C.tbd.CCH₃ or CH(OCH₃)₂.

More preferred compounds (7) include those of (4) wherein:

R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂ CN;

R₂ is C₃ to C₄ alkynyl, C₃ to C₆ cycloalkyl, C₂ to C₄ haloalkenyl, CH₂CH₂ F, CH₂ CH₂ Cl or CH₂ CH₂ Br;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, CH₂ CH₃, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

More preferred compounds (8) include those of (5) wherein:

R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂ CN;

R₂ is Q or CH₂ Q;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, CH₂ CH₃, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

More preferred compounds (9) include those of (6) wherein:

R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂ CN;

R₃ is C₁ to C₃ alkyl, C₃ to C₄ alkenyl, C₃ to C₄ alkynyl, C₃ to C₆cycloalkyl or C₁ to C₂ haloalkyl;

R₄ is C₂ to C₄ haloalkenyl or C₃ to C₄ epoxyalkyl;

X is CH₃, OCH₃, OCH₂ CH₃, Cl, OCF₂ H or OCH₂ CF₃ ; and

Y is CH₃, OCH₃, CH₂ CH₃, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.

Specifically preferred for reasons of greatest ease of synthesis and/orgreatest herbicidal efficacy are:

N-cyclopropyl-N'-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide,m.p. 197.5° to 199° C.(d); and

N-cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide,m.p. 184.5° to 185.5° C.(d).

DETAILED DESCRIPTION OF THE INVENTION

Synthesis

Compounds of Formula I can be prepared by one or more of the proceduresshown in Equations 1, 4, and 5. J, R, and A are as previously defined.

Equation 1 ##STR18##

The reaction of Equation 1 is best carried out in an inert aproticorganic solvent such as dichloromethane, 1,2-dichloroethane,tetrahydrofuran, or acetonitrile, at a temperature between 20° and 85°C. The order of addition is not critical; however, it is oftenconvenient to add the sulfonyl isocyanate or a solution of it in thereaction solvent, to a stirred suspension of the amine.

In some cases, the desired product is insoluble in the reaction solventat ambient temperature and crystallizes from it in pure form. Productssoluble in the reaction solvent are isolated by evaporation of thesolvent. Compounds of Formula I then may be purified by trituration ofthe evaporation residue with solvents such as 1-chlorobutane or ethylether and filtration, by recrystallization from mixtures of solventssuch as 1,2-dichloroethane, 1-chlorobutane and heptane or bychromatography on silica gel.

Sulfonyl isocyanates (II, W is O) are known in the art and are preparedfrom the corresponding sulfonamides (IV) by one of the following twogeneral methods.

Equation 2 ##STR19##

The sulfonamide IV is reacted with an alkyl isocyanate (e.g., n-butylisocyanate) in a solvent whose boiling point is above 135° C., such asxylene. The reaction can optionally be carried out in the presence of acatalytic amount of 1,4-diaza[2.2.2]-bicyclooctane (DABCO). The reactionmixture is heated to 135°-140° C. and held at that temperature for 5-60minutes, after which phosgene is slowly added at such a rate that thetemperature remains between 133° and 135° C. When the consumption ofphosgene has ceased, the mixture is cooled and filtered to removeinsoluble material. Finally, the solvent, alkyl isocyanate, and excessphosgene are evaporated, leaving the sulfonyl isocyanate (II).

If desired, the alkyl isocyanate-sulfonamide adduct can be made andisolated before reaction with the phosgene. In this case the sulfonamide(IV), alkyl isocyanate, and anhydrous base (e.g., K₂ CO₃) in a polar,aprotic solvent (e.g. acetone, butanone, or acetonitrile) are mixed andheated under reflux for 1 to 6 hours. The reaction mixture is thendiluted with water, and the pH is adjusted to about 3 with acid (e.g.HCl, H₂ SO₄). The adduct is filtered out and dried, and then reactedwith phosgene as described above. This procedure modification isespecially useful when sulfonamide (IV) is high melting and has lowsolubility in the phosgenation solvent.

Sulfonyl isocyanates (II, W is O) can also be prepared by the followingmethod.

Equation 3 ##STR20##

The sulfonamide (IV) is heated at reflux in an excess of thionylchloride. The reaction is continued until the sulfonamide protons are nolonger detectable in the proton magnetic resonance spectrum. From 16hours to 5 days is typically sufficient for complete conversion to thethionylamide (V) (Equation 3a).

The thionyl chloride is evaporated and the residue is treated with aninert solvent (e.g. toluene) containing at least one equivalent(typically 2-3 equivalents) of phosgene. A catalytic amount of pyridine(typically 0.1 equivalent) is added, and the mixture is heated to about60°-140° C., with 80°-100° C. preferred. Conversion to the isocyanate(II, W is O) is usually substantially complete within 15 minutes to 3hours (Equation 3b). The mixture is then cooled and filtered, and thesolvent is evaporated, leaving the sulfonyl isocyanate (II, W is O).

Sulfonyl isothiocyanates (II, W is S) are known in the art and areprepared from the corresponding sulfonamides (IV) by reaction withcarbon disulfide and potassium hydroxide followed by treatment of theresulting dipotassium salt VI with phosgene. Such a procedure isdescribed in Arch. Pharm. 299, 174 (1966).

Many of the compounds of Formula I can be prepared by the procedureshown in Equation 4.

Equation 4 ##STR21##

The reaction of Equation 4 is carried out by contacting phenylcarbamatesor phenylthiocarbamates of Formula VI with aminoheterocycles of FormulaIII in an inert organic solvent such as dioxane or tetrahydrofuran attemperatures of about 20°-100° C. for a period of about one-half totwenty-four hours. The product can be isolated by evaporation of thereaction solvent and purified by methods previously described.

Phenylcarbamates and phenylthiocarbamates of Formula VI can be preparedby the methods described, or modifications thereof known to thoseskilled in the art, in U.S. Pat. No. 4,443,243.

Alternatively, many of the compounds of Formula I can be prepared by themethod described in Equation 5.

Equation 5 ##STR22##

The reaction of Equation 5 can be carried out by contacting equimolaramounts of a sulfonamide of Formula IV with a heterocyclicphenylcarbamate or phenylthiocarbamate of Formula VII in the presence ofa base such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methodsanalogous to those described in South African Patent Application No.83/0441. The phenylcarbamates and phenylthiocarbamates of Formula VIIcan be prepared by methods, or modifications thereof known to thoseskilled in the art, described in South African Patent Application No.82/5671 and South African Patent Application No. 82/5045.

Sulfonamides of Formula IV can be prepared by one or more of theprocedures shown in Equations 6a, 6b, 6c, and 6d.

Equations 6a and 6b illustrate the reaction of sulfonyl chlorides ofFormula VIII with the appropriate primary and secondary amines to givesulfonamides of Formula IVa and IVb, respectively. Equations 6c and 6dillustrate the reaction of sulfonyl chlorides of Formulas IX and X withammonia to give sulfonamides of Formulas IVa and IVb, respectively.

Equation 6 ##STR23##

The reaction of Equations 6a, 6b, 6c, and 6d are best carried out in aninert aprotic solvent such as methylene chloride, tetrahydrofuran oracetonitrile at a temperature between -78° and 40° C. These reactionsrequire the presence of a scavenger for the by-product hydrochloricacid. This may be accomplished by the use of a two-fold excess of theamine or by the addition of an equivalent of a base such astriethylamine, pyridine, or aqueous sodium hydroxide. In cases in whichthe products are insoluble in the reaction solvent, they may be isolatedby simple filtration followed by washing with water to removehydrochloride salts. When the products are soluble, they can be isolatedby filtration to remove any insoluble salts, followed by evaporation ofthe solvent and trituration of the residue with solvents such as1-chlorobutane, diethyl ether or ethyl acetate, and filtration. In somecases it is helpful to wash the product with water to remove residualsalts.

Sulfonyl chlorides of Formula VIII where R₁ is as previously defined canbe prepared by the methods shown in Equations 7 and 8.

Diazotization of appropriately substituted aniline derivatives ofFormula XI, as shown in Equation 7, and subsequent coupling with sulfurdioxide in the presence of either cupric or cuprous chloride give thedesired products of Formula VIII. This reaction can be accomplished bymethods described, or modifications thereof, known to those skilled inthe art, in the Journal of Pharmacy and Pharmacology, Vol. 12, pages 648to 655 (1960).

Equation 7 ##STR24##

The reaction of Equation 7 can be accomplished by analogous methodsdescribed in U.S. Pat. No. 4,310,346. In Equation 7, a substitutedaniline XI, wherein R₁ is not NR_(d) R_(e), in concentrated hydrochloricacid is treated with a solution of sodium nitrite in water at -5° to 5°C. After being stirred for 10-30 minutes at about 0° C., the solution isadded to a mixture of excess sulfur dioxide and a catalytic amount ofcupric or cuprous chloride in acetic acid at about 10° C. After stirringfor 0.25 to 24 hours at temperatures between 10° to 25° C., the solutionis poured into a large excess of ice-water. The sulfonyl chlorides VIIIcan be isolated by filtration, or by extraction into a solvent such asmethylene chloride or diethyl ether, followed by drying and evaporationof the solvent.

Oxidative chlorination of appropriately substituted arylthioethers ofFormula XII give the desired products of Formula VIII wherein R₁₃ is C₂to C₄ alkyl or benzyl and R₁ is not C₁ to C₃ alkylthio, C₁ to C₃alkylsulfinyl, C₁ to C₃ haloalkylthio, C₂ to C₃ alkylthioalkyl or C₂ toC₃ haloalkylthioalkyl.

Equation 8 ##STR25##

The reaction of Equation 8 can be carried out by treating a solution ofthe thioether XII in a solvent such as acetic acid in the presence of atleast 2.5 equivalents of water and at least 3.0 equivalents of chlorineat 0°-30° C. for 0.25 to 5 hours. The reaction is poured into ice-waterand the product is isolated by extraction with a suitable solvent suchas methylene chloride, dried, and the solvent evaporated to yield aproduct sufficiently pure to be carried directly on to the next step.

Sulfonyl chlorides of Formula IX and X in Equations 6c and 6d are knownin the art and can be prepared by analogous methods described in U.S.Pat. No. 4,310,346.

Aniline derivatives of Formula XI in Equation 7 can be prepared as shownin Equation 9 by reduction of the corresponding nitro compounds ofFormula XIII where R₁ is other than NO₂.

Equation 9 ##STR26##

The reduction reactions of Equation 9 can be accomplished by methodsknown in the literature by those skilled in the art. For details see,for example, U.S. Pat. No. 4,511,392 and references cited therein.

The nitro compounds of Formula XIII are well known in the art and can beprepared by methods such as those described in U.S. Pat. No. 4,120,691.

The arylthioethers of Formula XII in Equation 8 are known in the art andcan be prepared by methods described in U.S. Pat. No. 4,371,391.

The primary and secondary amines required for the reactions shown inEquations 6a and 6b, respectively, are known in the art or can beprepared by one skilled in the art using methods known in theliterature.

In cases where the required secondary amine is not readily available,and R_(a) and R_(b) are other than H, it is more convenient to preparesulfonamides of Formula IVb using the method of Equation 10.

Equation 10a illustrates the reaction of orthonitrobenzenesulfonylchlorides of Formula XIV with primary amines to give secondarysulfonamides of Formula XV which can then be alkylated as shown inEquation 10b to give tertiary sulfonamides of Formula XVI. R₁, R₃, andR₄ are as previously defined and B is an appropriate displaceablesubstituent such as Cl, Br, I, OSO₂ CH₃, OSO₂ CF₃, OSO₂ C₆ H₅ or OSO₂-p-CH₃ C₆ H₄.

Equation 10 ##STR27##

The reactions of Equation 10a can be carried out under the conditionsdescribed for the reactions of Equation 6. The reactions of Equation 10bare best carried out by the addition of a base such as triethylamine,DBU, or potassium carbonate to a solution of the secondary sulfonamideof Formula XV in an aprotic polar solvent such as acetonitrile orN,N-dimethylformamide at about -78° to 40° C. The alkylating agent isthen added and after an additional one-half to 24 hours at about 0°-100°C. the reaction mixture is added to water to precipitate the product.Solid products can be isolated by simple filtration. If necessary, theproducts can be extracted with a solvent such as ethyl acetate ormethylene chloride. The product is then isolated by drying andevaporation of the solvent and, when necessary, further purified bychromatography on silica gel.

Sulfonyl chlorides of Formula XIV are known in the art and can beprepared by methods described in U.S. Pat. No. 4,120,691. The nitrocompounds of Formula XVI can be converted to sulfonamides of Formula IVbby the methods described in Equations 7 and 9.

When R₁ is other than C₁ to C₃ alkylthio, C₁ to C₃ alkylsulfinyl, C₁ toC₃ haloalkylthio, C₂ to C₃ alkylthioalkyl or C₂ to C₃haloalkylthioalkyl, sulfonamides of Formula IVa wherein R₂ is C₃ to C₆epoxyalkyl and sulfonamides of Formula IVb wherein either or both R₃ andR₄ are C₃ to C₆ epoxyalkyl can be conveniently prepared by contactingthe corresponding alkenyl derivatives with an oxidizing agent such ashydrogen peroxide or meta-chloroperbenzoic acid using procedures whichare well known in the art.

In cases where R₂, R₃, or R₄ is C₁ to C₆ alkyl substituted with OSO₂ R₅,OC(O)R₅, OCO₂ R₅, OC(O)NR₁₁ R₁₂, or OP(O)(OR₅)₂ it is often moreconvenient to first prepare the corresponding sulfonamides of FormulasIVa and IVb or sulfonylureas of Formula I in which R₂, R₃, or R₄ is C₁to C₆ alkyl substituted with OH. The hydroxy group can then befunctionalized to give the desired derivatives using methods which arewell known in the art.

When R₁ is other than C₁ to C₃ alkylthio, C₁ to C₃ alkylsulfinyl, C₁ toC₃ haloalkylthio, C₂ to C₃ alkylthioalkyl or C₂ to C₃ haloalkylthioalkyland R₂, R₃, or R₄ is C₁ to C₆ alkyl substituted with S(O)_(n) R₇ and nis equal to 1 or 2, the sulfonamides (of Formulas IVa and IVb) orsulfonylureas (of Formula I) may also be prepared from the correspondingcompounds in which n is equal to 0 by contact with an oxidizing agentsuch as hydrogen peroxide or meta-chloroperbenzoic acid. The level ofoxidation may be controlled by the amount of oxidant used and by thereaction temperature according to procedures which are known in the art.

The heterocyclic amines of Formula III in Equations 1 and 4 above can beprepared by methods known in the literature, or simple modificationthereof, by one skilled in the art.

For a review of the synthesis and reactions of 2-amino- and2-methylaminopyrimidines III (A=A-1, Z=CH) see The Chemistry ofHeterocyclic Compounds, Vol. 16, Wiley-Interscience, New York (1962).For a review of the synthesis and reactions 2-amino- and2-methylamino-s-triazines III (A=A-1, Z=N) see The Chemistry ofHeterocyclic Compounds, Vol. 13, Wiley-Interscience, New York (1959), F.C. Schaefer, U.S. Pat. No. 3,154,537 and F. C. Schaefer and K. R.Huffman J. Org. Chem., 28, 1812 (1963).

EP-A No. 84,224 and W. Braker et al., J. Chem. Soc., 69, 3072 (1947)describes methods for preparing aminopyridines and triazines substitutedby acetal groups such as dialkoxymethyl or 1,3-dioxolan-2-yl.

South African Patent Application No. 83/7434 describes methods for thesynthesis of cyclopropylpyrimidines and triazines substituted by suchgroups as alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylaminoor alkoxyalkyl.

The 5,6-dihydrofuro[2.3-d]pyrimidine-2-amines, thecyclopenta[d]pyrimidines-2-amines (III, A is A-2) and the6,7-dihydro-5H-pyrano[2.3-d]pyrimidin-2-amines (III, A is A-3) can beprepared as described in EP-A No. 15,683. Thefuro[2.3-d]pyrimidin-2-amines (III, A is A-4) are described in U.S. Pat.No. 4,487,626.

Compounds of Formula III, where A is A-5, are described in U.S. Pat. No.4,496,392.

The amines of Formula III where A is A-6 can be prepared by methodstaught in South African Patent Application No. 82/5045, or by suitablemodifications that would be obvious to one skilled in the art.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by direct contactof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali or quaternary amine salt) with a solution containing the cationto be exchanged. This method is most effective when the desired saltcontaining the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble, e.g., a potassium sodium orcalcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is furtherillustrated by the following specific examples. Unless otherwiseindicated, temperatures are in degrees centigrade.

EXAMPLE 1 N-Cyclopropyl-1,2-benzenedisulfonamide

A solution of 1.28 g of 2-(aminosulfonyl)benzenesulfonyl chloride in 12ml of dry THF was cooled to -65° C. and a solution of 0.80 ml ofcyclopropylamine in 12 ml of dry THF added dropwise. The resultingmixture was allowed to warm to room temperature, filtered, and thefiltrate concentrated in vacuo. The solid residue was partitionedbetween water and ethyl acetate, the organic phase was separated, washedwith water, dried (MgSO₄), concentrated in vacuo, and the residuetriturated with 1-chlorobutane to provide 1.15 g ofN-cyclopropyl-1,2-benzenedisulfonamide as a white solid, m.p. 202°-203°C.

NMR(CDCl₃ /DMSO-d₆)δ: 0.7 (br d, 4H, --CH₂ CH₂ --); 2.2 (m, 1H, CH ofcyclopropane); 6.5 (br s, 1H, SO₂ NH cyclopropyl); 7.0 (br s, 2H, SO₂NH₂); 7.7-7.9 (m, 2H, aromatics); and 8.2-8.4 (m, 2H, aromatics).

EXAMPLE 2N-Cyclopropyl-N'-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide

To a solution of 0.14 g of the product of Example 1 and 0.15 g ofphenyl(4,6-dimethoxypyrimidin-2-yl)carbamate in 2 ml of dry acetonitrilewas added 0.1 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU). Thesolution was stirred for 15 minutes at room temperature, diluted with 2ml of water and acidified with 5% hydrochloric acid. The precipitatedproduct was collected by filtration, washed successively with water,diethyl ether, and 1-chlorobutane, and dried in vacuo at 40° C. toafford 0.19 g of the subject compound, m.p. 197.5°-199° C. (dec.).

NMR(CDCl₃)δ: 0.6 (m, 4H, --CH₂ CH₂ --); 2.15 (m, 1H, CH ofcyclopropane); 3.98 (s, 6H, OCH₃ 's); 5.76 (s, 1H, pyr. C₅ --H); 6.16(br s, 1H, SO₂ NH cyclopropyl); 7.19 (br s, 1H, --SO₂ NHCONH--); 7.8 (m,2H, aromatics); 8.26 (m, 1H, aromatic); 8.58 (m, 1H, aromatic); and 12.7(br s, 1H, --SO₂ NHCO--).

IR(nujol) 1705 cm⁻¹ (C═O).

Using the methods described herein, the compounds of Tables I through IVcan be prepared. ##STR28##

                                      TABLE I                                     __________________________________________________________________________    Formula I, W = 0                                                              R  R.sub.1                                                                              R.sub.2         X        X        Z  m.p. (°C.)              __________________________________________________________________________    H  H       -n-C.sub.5 H   OCH.sub.3                                                                              CH.sub.3 N                                 H  H       -n-C.sub.5 H   OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H       -n-C.sub.5 H   Cl       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                          CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                          CH.sub.3 OC.sub.2 H.sub.5                                                                       CH                                H  H      CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                 OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                 OCH.sub.3                                                                              CH.sub.3 CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 (CH.sub.3).sub.2                                                   OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                                                        OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH(CH.sub.3)CH.sub.2 CH.sub.l CH CH.sub.3                                                     OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH(CH.sub.3)CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH═CH.sub.2                                                    Cl       OC.sub.2 H.sub.5                                                                       CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH═CH.sub.2                                                    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH═CH.sub.2                                                    CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CH═CF.sub.2 OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH═CF.sub.2 CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CCl═CHCl                                                                         CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CCl═CHCl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CCl═CHCl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CCl═CHCl                                                                         Cl       OC.sub.2 H.sub.5                                                                       CH                                H  H      CH.sub.2 CH═CHCF.sub.3                                                                    CH.sub.3 CH.sub.3 CH                                H  H      CH.sub.2 CH═CHCF.sub.3                                                                    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH═CHCH.sub.2 CH 2Cl                                                    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH═CHCH.sub.2 CH.sub.2 Cl                                               OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd. CH                                                                            OCH.sub.3                                                                              OCH.sub.3                                                                              CH 206-207(d)                     H  H      CH.sub.2 C.tbd.CH                                                                             Cl       OCH.sub.3                                                                              CH 207.5-209(d)                   H  H      CH.sub.2 CH.sub.2 C.tbd.CH                                                                    CH.sub.3 OCH.sub.3                                                                              CH 199-200(d)                     H  H      CH.sub.2 C.tbd.CH                                                                             CH.sub.3 CH.sub.3 201-203(d)                        H  H      CH.sub.2 C.tbd.CH                                                                             CH.sub.3 OCH.sub.3                                                                              N  198-201(d)                     H  H      CH.sub.2 C.tbd.CH                                                                             CH.sub.3 CH.sub.3 N  187-189(d)                     H  H      CH.sub.2 C.tbd.CH                                                                             OCH.sub.3                                                                              C.tbd.CH N                                 H  H      CH.sub.2 C.tbd.CH                                                                             Br       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd.CH                                                                             Br       NHCH.sub.3                                                                             CH                                H  H      CH.sub.2 C.tbd.CH                                                                             CH.sub.3 N(CH.sub.3).sub.2                                                                      CH                                H  H      CH.sub.2 C.tbd.CH                                                                             OC.sub.2 H.sub.5                                                                       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd.CH                                                                             OCH.sub.3                                                                              C.sub.2 H.sub.5                                                                        CH                                H  H      CH.sub.2 C.tbd.CCH.sub.3                                                                      OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 C.tbd.CCH.sub.3                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 C.tbd.CCH.sub.3                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd.CCH.sub.3                                                                      CH.sub.3 H        CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 C.tbd.CH                                                           OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 C.tbd.CH                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 C.tbd.CCH.sub.2 CH.sub.3                                                    OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 C.tbd.CCH.sub.2 CH.sub.3                                                    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      cyclopropyl     H        H        CH                                H  H      cyclopropyl     CH.sub.3 H        CH                                H  H      cyclopropyl     CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                    CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 CH.sub.2 CF.sub.3                                                             CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 CF.sub.3                                                                      CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 CH.sub.2 Cl                                                                   CH.sub.3 CH                                H  H      cyclopropyl     CF.sub.3 CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 Cl                                                                            CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 Br                                                                            CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.2 F                                                                             CH.sub.3 CH                                H  H      cyclopropyl     CH.sub.3 CH.sub.3 CH 190-192(d)                     H  H      cyclopropyl     OCH.sub.3                                                                              CH.sub.3 CH  192-193.5(d)                  H  H      cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH 197.5-199(d)                   H  H      cyclopropyl     F        OCH.sub.3                                                                              CH                                H  H      cyclopropyl     Cl       OCH.sub.3                                                                              CH 210-213(d)                     H  H      cyclopropyl     Br       OCH.sub.3                                                                              CH                                H  H      cyclopropyl     I        OCH.sub.3                                                                              CH                                H  H      cyclopropyl     Cl       OC.sub.2 H.sub.5                                                                       CH                                H  H      cyclopropyl     Cl       N(OCH.sub.3)CH.sub.3                                                                   CH                                H  H      cyclopropyl     Cl       NHCH.sub.3                                                                             CH                                H  H      cyclopropyl     Cl       N(CH.sub.3).sub.2                                                                      CH                                H  H      cyclopropyl     N(CH.sub.3).sub.2                                                                      N(CH.sub.3).sub.2                                                                      CH                                H  H      cyclopropyl     OC.sub.2 H.sub.5                                                                       CH.sub.3 CH                                H  H      cyclopropyl     O -n C.sub.4 H.sub.9                                                                   CH.sub.3 CH                                H  H      cyclopropyl     OCH.sub.2 CF.sub.3                                                                     CH.sub.3 CH                                H  H      cyclopropyl     OCH.sub.2 CH.sub.2 CH.sub.2 Cl                                                         CH.sub.3 CH                                H  H      cyclopropyl     SCH.sub.3                                                                              CH.sub.3 CH                                H  H      cyclopropyl     SC.sub.2 H.sub.5                                                                       CH.sub.3 CH                                H  H      cyclopropyl     SCH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       CH                                H  H      cyclopropyl     CH.sub.3 H        N                                 H  H      cyclopropyl     CH.sub.3 CH.sub.3 N                                 H  H      cyclopropyl     CH.sub.3 C.tbd.CH N                                 H  H      cyclopropyl     CH.sub.3 C.tbd.CCH.sub.3                                                                        N                                 H  H      cyclopropyl     CH.sub.3 Cl       N                                 H  H      cyclopropyl     CH.sub.3 CH.sub.2 CH.sub.2 Cl                                                                   N                                 H  H      cyclopropyl     CH.sub.3 CH.sub.2 OCH.sub.3                                                                     N                                 H  H      cyclopropyl     CH.sub.3 CH.sub. 2`OC.sub.2 H.sub.5                                                             N                                 H  H      cyclopropyl     CH.sub.3 SCH.sub.3                                                                              N                                 H  H      cyclopropyl     CH.sub.3 O -n C.sub.4 H.sub.9                                                                   N                                 H  H      cyclopropyl     CH.sub.3 OCH.sub.3 CH═CH.sub.2                                                              N                                 H  H      cyclopropyl     CH.sub.3 OCH.sub.3 C.tbd.CCH.sub.3                                                              N                                 H  H      cyclopropyl     CH.sub.3 CH.sub.2 SCH.sub.3                                                                     N                                 H  H      cyclopropyl     CH.sub.3 CF.sub.3 CH                                H  H      cyclopropyl     CH.sub.3 OCH.sub.3                                                                              N  184.5-185.5(d)                 H  H      cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              N  190-192(d)                     H  H      cyclopropyl     OCH.sub.3                                                                              cyclopropyl                                                                            CH                                H  H      cyclopropyl     OCH.sub.3                                                                              OCF.sub.3                                                                              CH                                H  H      cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH 195.5-197(d)                   H  H      cyclobutyl      Cl       OCH.sub.3                                                                              CH 214.5-217(d)                   H  H      cyclobutyl      CH.sub.3 OCH.sub.3                                                                              CH  191-192.5(d)                  H  H      cyclobutyl      CH.sub.3 CH.sub.3 CH 180-184(d)                     H  H      cyclobutyl      CH.sub.3 N(C.sub.2 H.sub.5).sub.2                                                               CH                                H  H      cyclobutyl      CH.sub.3 NHCH.sub.2 CH.sub.2 CH.sub.3                                                           CH                                H  H      cyclobutyl      CH.sub.3 COCH.sub.3                                                                             CH                                H  H      cyclobutyl      CH.sub.3 CH(OCH.sub.3).sub.2                                                                    CH                                H  H      cyclobutyl      CH.sub.3 1,3-dioxolan-2-yl                                                                      CH                                H  H      cyclobutyl      CH.sub.3 1,3-oxathian-2-yl                                                                      CH                                H  H      cyclobutyl      NH.sub.2 CH.sub.3 N                                 H  H      cyclobutyl      SCH.sub.2 CH.sub.2 Cl                                                                  CH.sub.3 N                                 H  H      cyclobutyl      CH.sub.2 OC.sub.2 H.sub.7                                                              CH.sub.3 N                                 H  H      cyclobutyl      OC.sub.2 H.sub.5 OCH.sub.3                                                             CH.sub.3 CH                                H  H      cyclobutyl      OCH.sub.3                                                                              CH.sub.3 N  190-192(d)                     H  H      cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              N   191-192.5(d)                  H  H      cyclobutyl      CH.sub.3 CH.sub.3 N                                 H  H      cyclobutyl      OCH.sub.3                                                                              C.tbd.CH N                                 H  H      cyclobutyl      CH.sub.3 SCH.sub.3                                                                              N                                 H  H      cyclopentyl     OCH.sub.3                                                                              CH.sub.3 CH 182.5-183.5(d)                 H  H      cyclopentyl     OCH.sub.3 OCH.sub.3                                                                    CH.sub.3 CH                                H  H      cyclopentyl     OCH.sub.2 CH.sub.2 OCH.sub.3                                                           CH.sub.3 CH                                H  H      cyclopentyl     NH.sub.2 CH.sub.3 CH                                H  H      cyclopentyl     CH.sub.3 CH.sub.3 CH 190-192(d)                     H  H      cyclopentyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH  187-188.5(d)                  H  H      cyclopentyl     Cl       OCH.sub.3                                                                              CH  214-215.5(d)                  H  H      cyclopentyl     SCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      cyclopentyl     OCH.sub.3                                                                              OCH.sub.3                                                                              N  193-195(d)                     H  H      cyclopentyl     CH.sub.3 OCH.sub.3                                                                              N  180-182(d)                     H  H      cyclopentyl     CH.sub.3 CH.sub.3 N                                 H  H      cyclopentyl     CH.sub.3  -n-C.sub.4 H.sub.9                                                                    N                                 H  H      cyclohexyl      CH.sub.3 CH.sub.3 N                                 H  H      cyclohexyl      CH.sub.3 OCH.sub.3                                                                              N                                 H  H      cyclohexyl      OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      cyclohexyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      cyclohexyl      Cl       OCH.sub.3                                                                              CH                                H  H      cyclohexyl      CH.sub.3 OCH.sub.3                                                                              CH                                H  H      cyclohexyl      CH.sub.3 CH.sub.3 CH                                H  H      3-CH.sub.3 -cyclopentyl                                                                       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      3-CH.sub.3 -cyclopentyl                                                                       OCH.sub.3                                                                              CH.sub.3 N                                 H  H      4-CH.sub.3 -cyclohexyl                                                                        OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      4-CH.sub.3 -cyclohexyl                                                                        CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 -cyclopropyl                                                                         CH.sub.3 CH.sub.3 N                                 H  H      CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              CH.sub.3 N  182-184                        H  H      CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              N  184-186                        H  H      CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH 171-173                        H  H      CH.sub.2 -cyclopropyl                                                                         CH.sub.3 OCH.sub.3                                                                              CH 173-176                        H  H      CH.sub.2 -cyclopropyl                                                                         Cl       OCH.sub.3                                                                              CH 207-209                        H  H      CH.sub.2 -cyclopropyl                                                                         CH.sub.3 CH.sub.3 CH 186-188                        H  H      cyclohexen-1-yl CH.sub.3 OCH.sub.3                                                                              N                                 H  H      cyclohexen-1-yl OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -oxirane                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                              CH 184-185(d)                     H  H      CH.sub.2 -oxirane                                                                             Cl       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -oxirane                                                                             CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -oxirane                                                                             CH.sub.3 CH.sub.3 N                                 H  H      CH.sub.2 -oxirane                                                                             CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 -oxirane                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 -oxirane                                                                             OCH.sub.3                                                                              C.tbd.CH N                                 H  H      CH.sub.2 CH.sub.2 F                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              N   178-179.5(d)                  H  H      CH.sub.2 CH.sub.2 F                                                                           CH.sub.3 OCH.sub.3                                                                              N  192.5-194(d)                   H  H      CH.sub.2 CH.sub.2 F                                                                           Cl       OCH.sub.3                                                                              CH 205-208(d)                     H  H      CH.sub.2 CH.sub.2 F                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              CH 199.5-201(d)                   H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCH.sub.3                                                                              CH.sub.3 CH                                H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 Br                                                                          OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 Br                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub. 2 CH(OCH.sub.3).sub.2                                                                 CH.sub.3 OCH.sub.3                                                                              N  174-175(d)                     H  H      CH.sub.2 CH(OCH.sub.3).sub.2                                                                  OCH.sub.3                                                                              OCH.sub.3                                                                              CH 193.5-195(d)                   H  H      CH.sub.2 CH(OC.sub.2 H.sub.5).sub.2                                                           OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH(OC.sub.2 H.sub.5).sub.2                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -1,3-dioxan-2-yl                                                                     CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 -1,3-dioxan-2-yl                                                                     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      OCH.sub.3       CH.sub.3 OCH.sub.3                                                                              N  205-206(d)                     H  H      OCH.sub.3       OCH.sub.3                                                                              OCH.sub.3                                                                              CH 209-211(d)                     H  H      C.sub.6 H.sub.5 OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      C.sub.5 H.sub.5 CH.sub.3 OCH.sub.3                                                                              N                                 H  H      2-CH.sub.3 --C.sub.6 H.sub.4                                                                  OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      2-CH.sub.3 --C.sub.6 H.sub.4                                                                  OCH.sub.3                                                                              CH.sub.3 N                                 H  H      2-Cl--C.sub.6 H.sub.4                                                                         OCH.sub.3                                                                              CH.sub.3 N                                 H  H      2-Cl--C.sub.6 H.sub.4                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      4-Br--C.sub.6 H.sub.4                                                                         CH.sub.3 OCH.sub.3                                                                              N                                 H  H      4-Br--C.sub.6 H.sub.4                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      3-CF.sub.3 --C.sub.6 H.sub.4                                                                  OCH.sub.3                                                                              CH.sub.3 N                                 H  H      3-CF.sub.3 --C.sub.6 H.sub.4                                                                  OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      4-CH.sub.3 O--C.sub.6 H.sub.4                                                                 OCH.sub.3                                                                              CH.sub.3 N                                 H  H      4-CH.sub.3 O--C.sub.6 H.sub.4                                                                 OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH 198-199(d)                     H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3 OCH.sub.3                                                                              CH 180-182(d)                     H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      Cl       OCH.sub.3                                                                              CH  168-170.5(d)                  H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3 CH.sub.3 CH 199-201(d)                     H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3 CH.sub.3 N                                 H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              CH.sub.3 N  160.5-162.5(d)                 H  H      CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              N  173-175(d)                     H  H      CH.sub.2 COCH.sub.3                                                                           OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 COCH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CN              OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CN              OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 OH                                                                          OCH.sub.3                                                                              CH.sub.3 N  175-178(d)                     H  H      CH.sub.2 CH.sub.2 OH                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH 148-151(d)                     H  H      CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                               CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 OC(O)CH.sub.3                                                               OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                           CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 S.sub.2 OCH.sub.3                                                           OCH.sub.3                                                                              CH                                         H  H      CH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                                                    OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 C(O)N(CH.sub.3).sub.2                                              CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 C(O)N(CH.sub.3).sub.2                                              OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 OP(O)(OCH.sub.3).sub.2                                    OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub. 2 CH.sub.2 CH.sub.2 OP(O)(OCH.sub.3).sub.2                                   OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                          OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 SCH.sub.3                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3                                                  OCH.sub.3                                                                              CH.sub.3 N                                 H  H      CH.sub.2 CH.sub.2 CH.sub.2 So.sub.2 CH.sub.3                                                  OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      1,3-dithiolan-2-yl                                                                            CH.sub.3 OCH.sub.3                                                                              N                                 H  H      1,3-dithiolan-2-yl                                                                            OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -tetrahydrofuran-2-yl                                                                OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -tetrahydrofuran-2-yl                                                                CH.sub.3 OCH.sub.3                                                                              N                                 H  H      4,6-dimethoxypyrimidin-2-yl                                                                   CH.sub.3 OCH.sub.3                                                                              CH                                H  H      4-picolyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  3-CH.sub.3                                                                            -n-C.sub.5 H.sub.11                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  4-CH.sub.3                                                                            -n-C.sub.5 H.sub.11                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-C.sub.2 H.sub.5                                                                     -n-C.sub.5 H.sub.11                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-CF.sub.3                                                                           CH.sub.2 -cyclpropyl                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-CH.sub.2 CH.sub.2 Cl                                                               CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-Cl   CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-Br   CH.sub.2 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-F    CH.sub.3 -cyclopropyl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-NO.sub.2                                                                           cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-OCH.sub.3                                                                          cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-SO.sub.2 NHCH.sub.3                                                                cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-SCH.sub.3                                                                          cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-SOC.sub.2 H.sub.5                                                                  cyclobutyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-SO.sub.2 C.sub.2 H.sub.5                                                           CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-CN   CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CH.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CH.sub.2 CF.sub.3                                                                  CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CF.sub.3                                                                           CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-SCH.sub.2 F                                                                        CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-OCH.sub.2 CF.sub.3                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CO.sub.2 CH.sub.3                                                                  cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CO.sub.2 C.sub.2 H.sub.5                                                           cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CO.sub.2 CH.sub.2 CH═CH.sub.2                                                  cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CO.sub.2 CH.sub.2 CH.sub.2 CN                                                      cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CO.sub.2 -cyclohexyl                                                               cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-CH.sub.2 OCH.sub.3                                                                 cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-Cl   cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-SCH.sub.3                                                                          cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  6-OCH.sub.3                                                                          cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         6-OCH.sub.3                                                                          cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      cyclopropyl     CH.sub.3 OCH.sub.3                                                                              N                                 CH.sub.3                                                                         H      cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 CH.sub.3                                                                         H      CH.sub.2 C.tbd.CH                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      CH.sub.2 C.tbd.CH                                                                             CH.sub.3 OCH.sub.3                                                                              N                                 CH.sub.3                                                                         H      CH.sub.2 C.tbd.CH                                                                             Cl       OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      CH.sub.2 -cyclobutyl                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      CH.sub.2 -cyclobutyl                                                                          OCH.sub.3                                                                              CH.sub. 3                                                                              N                                 CH.sub.3                                                                         H      CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              CH.sub.3 N                                 CH.sub.3                                                                         H      CH.sub.2 C.sub.6 H.sub.5                                                                      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      CH.sub.2 -oxirane                                                                             OCH.sub.3                                                                              CH.sub.3 N                                 CH.sub.3                                                                         H      CH.sub.2 -oxirane                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                CH.sub.3                                                                         H      4-Cl--C.sub.6 H.sub.4                                                                         CH.sub.3 OCH.sub.3                                                                              N                                 CH.sub.3                                                                         H      4-Cl--C.sub.6 H.sub.4                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 F                                                                           CH.sub.3 CH.sub.3 CH 188-190(d)                     H  H      CH.sub.2 CH.sub.2 F                                                                           CH.sub.3 OCH.sub.3                                                                              CH  192-193.5(d)                  H  H      CH.sub.2 CH.sub.2 Cl                                                                          CH.sub.3 CH                                         H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCH.sub.3                                                                              CH                                         H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 Br                                                                          CH.sub.3 CH.sub.3 CH                                H  H      CH.sub.2 CH.sub.2 Br                                                                          CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 Br                                                                          Cl       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 Br                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH(OCH.sub.3).sub.2                                                                  CH.sub.3 CH.sub.3 CH   185-186.5(d)                 H  H      CH.sub.2 CH(OCH.sub.3).sub.2                                                                  CH.sub.3 OCH.sub.3                                                                              CH  187-188.5(d)                  H  H      CH.sub.2 CH(OCH.sub.3).sub.2                                                                  Cl       OCH.sub.3                                                                              CH 180-182(d)                     H  H      CH.sub.2 CH(OCH.sub.3).sub.2                                                                  OCH.sub.3                                                                              OCH.sub.3                                                                              N  176-178(d)                     H  H      CH.sub.2 COCH.sub.3                                                                           CH.sub.3 CH.sub.3 CH                                H  H      CH.sub.2 COCH.sub.3                                                                           CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CH.sub.2 COCH.sub.3                                                                           Cl       OCH.sub.3                                                                              CH                                H  H      CH.sub.2 COCH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CN              CH.sub.3 CH.sub.3 CH                                H  H      CN              CH.sub.3 OCH.sub.3                                                                              CH                                H  H      CN              Cl       OCH.sub.3                                                                              CH                                H  H      CN              OCH.sub.3                                                                              OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 CH.sub.3 CH 177-179(d)                     H  H      CH.sub.2 CH.sub.2 OH                                                                          CH.sub.3 OCH.sub.3                                                                              CH 163-165(d)                     H  H      CH.sub.2 CH.sub.2 OH                                                                          Cl       OCH.sub.3                                                                              CH 151-153(d)                     H  H      CH.sub.2 CH.sub.2 OH                                                                          OCH.sub.3                                                                              OCH.sub.3                                                                              N  >250                           H  H      OCH.sub.3       CH.sub.3 CH.sub.3 CH 212.5-213(d)                   H  H      OCH.sub.3       CH.sub.3 OCH.sub.3                                                                              CH 206-208(d)                     H  H      OCH.sub.3       Cl       OCH.sub.3                                                                              CH 225-227(d)                     H  H      OCH.sub.3       OCH.sub.3                                                                              OCH.sub.3                                                                              N  197-199(d)                     H  H      Thiazol-2-yl    OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      Thiazol-2-yl    CH.sub.3 OCH.sub.3                                                                              N                                 H  H      1,3,4-Thiadiazol-2-yl                                                                         OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      1,3,4-Thiadiazol-2-yl                                                                         CH.sub.3 OCH.sub.3                                                                              N                                 H  H      2-Picolyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      2-Picolyl       CH.sub.3 OCH.sub.3                                                                              N                                 H  H      3-Picolyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      3-Picolyl       CH.sub.3 OCH.sub.3                                                                              N                                 H  H      2-Pyridyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      2-Pyridyl       CH.sub.3 OCH.sub.3                                                                              N                                 H  H      3-Pyridyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      3-Pyridyl       CH.sub.3 OCH.sub.3                                                                              N                                 H  H      4-Pyridyl       OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      4-Pyridyl       CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 -Pyridin-2-yl                                                               OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 -Pyridin-2-yl                                                               CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 -1-Methylpyrrolidin-2-yl                                                             OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -1-Methylpyrrodidin-2-yl                                                             CH.sub.3 OCH.sub.3                                                                              N                                 H  H      CH.sub.2 CH.sub.2 -1-Methylpyrrol-2-yl                                                        OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 -1-Methylpyrrol-2-yl                                                        CH.sub.3 OCH.sub.3                                                                              N                                 H  5-OCH.sub.2 CF.sub.3                                                                 cyclopropyl     CH.sub.3 CH.sub.3 CH                                H  5-OCH.sub.2 CF.sub.3                                                                 cyclopropyl     CH.sub.3 OCH.sub.3                                                                              CH                                H  5-OCH.sub.2 CF.sub.3                                                                 cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-OCH.sub.2 CF.sub.3                                                                 cyclopropyl     CH.sub.3 OCH.sub.3                                                                              N                                 H  5-OCH.sub.2 CF.sub.3                                                                 cyclopropyl     Cl       OCH.sub.3                                                                              CH                                H  5-CH.sub.2 OCH.sub.2 CF.sub.3                                                        cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-CH.sub.2 CN                                                                        cyclopropyl     OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  5-N(CH.sub.3).sub.2                                                                  cyclpropyl      OCH.sub.3                                                                              OCH.sub.3                                                                              CH                                H  H      CH.sub.2 -Pyridin-4-yl                                                                        CH.sub.3 CH.sub.3 CH 177-179                        H  H      CH.sub.2 -Pyridin-4-yl                                                                        CH.sub.3 OCH.sub.3                                                                              CH 172-174                        H  H      CH.sub.2 -Pyridin-4-yl                                                                        OCH.sub.3                                                                              OCH.sub.3                                                                              CH 164-165                        H  H      CH.sub.2 -Pyridin-4-yl                                                                        CH.sub.3 OCH.sub.3                                                                              N  177-178                        H  H      CH.sub.2 -Pyridin-4-yl                                                                        OCH.sub.3                                                                              OCH.sub.3                                                                              N  174-177                        H  H      CH.sub.2 -Pyridin-4-yl                                                                        Cl       OCH.sub.3                                                                              CH 180-181                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 CH.sub.3 CH.sub.3 CH 160-162                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 CH.sub. 3                                                                              OCH.sub.3                                                                              CH 180-181                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 OCH.sub.3                                                                              OCH.sub.3                                                                              CH 163-165                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 CH.sub.3 OCH.sub.3                                                                              N  159-160                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 OCH.sub.3                                                                              OCH.sub.3                                                                              N  170-172                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 Cl       OCH.sub.3                                                                              CH 193-195                        H  H      CH.sub.2 CH.sub.2 CH.sub.2 Br                                                                 CH.sub.3 OCH.sub.3                                                                              CH 132-134(d)                     H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCF.sub.2 H                                                                            CH.sub.3 CH                                H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCF.sub.2 H                                                                            OCH.sub.3                                                                              CH                                H  H      CH.sub.2 CH.sub.2 Cl                                                                          OCF.sub.2 H                                                                            OCF.sub.2 HCH                              H  H      cyclobutyl      OCF.sub.2 H                                                                            OCF.sub.2 H                                                                            CH                                H  H      cyclobutyl      OCF.sub.2 H                                                                            SCH.sub.3                                                                              CH                                H  H      cyclobutyl      OCF.sub.2 H                                                                            N(CH.sub.3).sub.2                                                                      CH                                H  H      cyclobutyl      OCF.sub.2 H                                                                            C.tbd.CH CH                                H  H      cyclobutyl      OCF.sub.2 H                                                                            1,3-dioxan-2-yl                                                                        CH                                H  H      CH.sub.2 CF.sub.3                                                                             OCF.sub.2 H                                                                            H        CH                                H  H      CH.sub.2 CF.sub.3                                                                             OCF.sub.2 H                                                                            C.sub.2 H.sub.5                                                                        CH                                H  H      CH.sub.2 CF.sub.3                                                                             OCF.sub.2 H                                                                            OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            OCH.sub.3                                                                              CH                                H  H      CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            CH.sub.3 CH                                H  H      CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            CH.sub.2 OCH.sub.3                                                                     CH                                H  5-OCH.sub.3                                                                          CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            CH.sub.3 CH                                H  5-Br   CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            CH.sub.3 CH                                CH.sub.3                                                                         H      CH.sub.2 C.tbd.CH                                                                             OCF.sub.2 H                                                                            CH.sub.3 CH                                __________________________________________________________________________

                  TABLE Ia                                                        ______________________________________                                        Formula I, W = S                                                              R   R.sub. 1                                                                              R.sub. 2     X     Y     Z    m.p.(°C.)                    ______________________________________                                        H   H       CH.sub.2 C.tbd.CH                                                                          CH.sub.3                                                                            OCH.sub.3                                                                           N                                        H   H       CH.sub.2 C.tbd.CH                                                                          OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       cyclopropyl  CH.sub.3                                                                            OCH.sub.3                                                                           CH                                       H   H       cyclopropyl  OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       CH.sub.2 CH.sub.2 F                                                                        OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       CH.sub.2 CH.sub.2 F                                                                        CH.sub.3                                                                            OCH.sub.3                                                                           N                                        H   H       CH.sub.2 CH.sub.2 Cl                                                                       Cl    OCH.sub.3                                                                           CH                                       H   H       CH.sub.2 CH.sub.2 Cl                                                                       OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       OCH.sub.3    CH.sub.3                                                                            OCH.sub.3                                                                           CH                                       H   H       OCH.sub.3    OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       OC.sub.2 H.sub.5                                                                           CH.sub.3                                                                            OCH.sub.3                                                                           N                                        H   H       OC.sub.2 H.sub.5                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   H       CH.sub.2 -cyclopropyl                                                                      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                       H   H       CH.sub.2 -cyclopropyl                                                                      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       H   OCH.sub.3                                                                             CH.sub.2 CH.sub.2 F                                                                        OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                       ______________________________________                                    

                                      TABLE II                                    __________________________________________________________________________    Formula II, W = O                                                                                                    m.p.                                   R  .sup.R 1                                                                            .sup.R 2  A  .sup.X 1                                                                           .sup.X 2                                                                          Y .sup.Y 1                                                                         .sup.Y 2                                                                         (°C.)                           __________________________________________________________________________    H  H      -n-C.sub.6 H.sub.13                                                                    A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H      -n-C.sub.6 H.sub.13                                                                    A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  H      -n-C.sub.6 H.sub.13                                                                    A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-2                                                                              OCF.sub. 2 H                                                                       --  --                                                                              O  --                                        H  H     cyclopropyl                                                                             A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              CH.sub.2                                                                         --                                        H  H     cyclopropyl                                                                             A-2                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              CH.sub.2                                                                         --                                        H  H     cyclopropyl                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     cyclopropyl                                                                             A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  H     cyclopropyl                                                                             A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H     cyclopropyl                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  H     cyclopropyl                                                                             A-2                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              O  --                                        H  H     cyclopropyl                                                                             A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              O  --                                        H  H     cyclobutyl                                                                              A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     cyclobutyl                                                                              A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  H     cyclobutyl                                                                              A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              O  --                                        H  H     cyclobutyl                                                                              A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 -cyclopropyl                                                                   A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 -cyclopropyl                                                                   A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H     CH.sub.2 -oxirane                                                                       A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 -oxirane                                                                       A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              O  --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H     2-BrC.sub.6 H.sub.4                                                                     A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        H  H     2-BrC.sub.6 H.sub.4                                                                     A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  5-Cl  CH.sub.2 C.sub.6 H.sub.5                                                                A-2                                                                              OCF.sub.2 H                                                                        --  --                                                                              O  --                                        H  6-SO.sub.2 CH.sub.3                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                        H  5-Cl  cyclopropyl                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                        H  6-Cl  cyclopropyl                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  5-OCH.sub.3                                                                         cyclopropyl                                                                             A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                        CH.sub.3                                                                         H     cyclopropyl                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                        H  H      -n-C.sub.5 H.sub.11                                                                    A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  H     CH.sub.2 C.tbd.CH                                                                       A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     CH.sub.2 C.sub.6 H.sub.5                                                                A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  H     CH.sub.2 C.sub.6 H.sub.5                                                                A-3                                                                              OCF.sub.2 H                                                                        --  --                                                                              -- --                                        H  H     cyclopropyl                                                                             A-3                                                                              OCF.sub.2 H                                                                        --  --                                                                              -- --                                        H  H     cyclopropyl                                                                             A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     CH.sub.2 -oxirane                                                                       A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     CH.sub.2 -oxirane                                                                       A-3                                                                              OC.sub. 2 H.sub.5                                                                  --  --                                                                              -- --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-3                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              -- --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-3                                                                              OCF.sub.2 H                                                                        --  --                                                                              -- --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     4-CH.sub.3 --C.sub.6 H.sub.4                                                            A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  H     4-CH.sub.3 --C.sub.6 H.sub.4                                                            A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  5-OCH.sub.3                                                                         cyclobutyl                                                                              A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  6-OCH.sub.3                                                                         cyclobutyl                                                                              A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        H  6-Cl  cyclobutyl                                                                              A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        H  6-SCH.sub.3                                                                         cyclobutyl                                                                              A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                        CH.sub.3                                                                         H     cyclobutyl                                                                              A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                        CH.sub.3                                                                         H     CH.sub. 2 -cyclopropyl                                                                  A-3                                                                              OCF.sub.2 H                                                                        --  --                                                                              -- --                                        H  H     CH.sub.2 -cyclopropyl                                                                   A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                  H  H     CH.sub.2 -cyclopropyl                                                                   A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                         H  H     cyclopropyl                                                                             A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- CH.sub.3                                  H  H     cyclopropyl                                                                             A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                  H  H     cyclopropyl                                                                             A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                         H  H     cyclopropyl                                                                             A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                         H  H     CH.sub.2 CH.sub.2 CH═CH.sub.2                                                       A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                         H  H     CH.sub.2 CH.sub.2 CH═CH.sub.2                                                       A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                         H  H     CH.sub.2 CF.sub.3                                                                       A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                         H  H     CH.sub.2 CF.sub.3                                                                       A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                  H  H     CH.sub.2 C.sub.6 H.sub.5                                                                A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                         H  5-CH.sub.3                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                         H  5-SCH.sub.3                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                  H  6-OCH.sub.3                                                                         CH.sub.2 C.sub.6 H.sub.5                                                                A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- CH.sub.3                                  CH.sub.3                                                                         H     CH.sub.2 C.sub.6 H.sub.5                                                                A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                         CH.sub.3                                                                         H     CH.sub.2 C.tbd.CH                                                                       A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                         H  H     CH.sub.2 CF.sub.3                                                                       A-5                                                                              --   CH.sub.3                                                                          --                                                                              -- --                                        H  H     CH.sub.2 CF.sub.3                                                                       A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                        H  H     cyclopropyl                                                                             A-5                                                                              --   CH.sub.3                                                                          --                                                                              -- --                                        H  H     cyclopropyl                                                                             A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                        H  H     CH.sub.2 C.sub.6 H.sub.5                                                                A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                        H  5-CH.sub.3 O                                                                        CH.sub.2 C.sub.6 H.sub.5                                                                A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                        CH.sub.3                                                                         H      -n-C.sub.5 H.sub.11                                                                    A-5                                                                              --   OCH.sub. 3                                                                        --                                                                              -- --                                        __________________________________________________________________________

                                      TABLE IIa                                   __________________________________________________________________________    Formula II, W = S                                                                                             m.p.                                          R R.sub. 1                                                                        R.sub. 2 A  X.sub. 1                                                                          X.sub. 2                                                                          Y Y.sub. 1                                                                         Y.sub. 2                                                                         (°C.)                                  __________________________________________________________________________    H H CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                         --  --                                                                              O  --                                               H H CH.sub.2 CH.sub.2 F                                                                    A-2                                                                              OCH.sub.3                                                                         --  --                                                                              CH.sub.2                                                                         --                                               H H cyclopropyl                                                                            A-3                                                                              CH.sub.3                                                                          --  --                                                                              -- --                                               H H CH.sub.2 CH.sub.2 F                                                                    A-3                                                                              OCH.sub.3                                                                         --  --                                                                              -- --                                               H H CH.sub.2 CH.sub.2 Cl                                                                   A-4                                                                              CH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                         H H CH.sub.2 C.tbd.CH                                                                      A-4                                                                              OCH.sub.3                                                                         --  --                                                                              -- H                                                H H CH.sub.2 -cyclopropyl                                                                  A-5                                                                              --  OCH.sub.3                                                                         --                                                                              -- --                                               H H CH.sub.2 CH.sub.2 F                                                                    A-5                                                                              --  OCH.sub.3                                                                         --                                                                              -- --                                               __________________________________________________________________________

                                      TABLE III                                   __________________________________________________________________________    Formula III, W = 0                                                            R  R.sub.1    R.sub.3     R.sub.4        X   Y        Z  m.p.                 __________________________________________________________________________                                                             (°C.)         H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CF.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 CH(OC.sub.2 H.sub.5).sub.2                                                          CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH(OC.sub.2 H.sub.5).sub.2                                                          CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 -1,3-dioxan-2-yl                                                                    CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 -1,3-dioxan-2-yl                                                                    OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH═CH--CF.sub.3                                                                 OCH.sub.3                                                                         CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH═CH--CF.sub.3                                                                 OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            OCH.sub.3                                                                         OHC.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 -oxirane                                                                            OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CH.sub.2 C(O)CH.sub.3                                                                        OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 OC(O)CH.sub.2                                      CH.sub.3       OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 OSO.sub.2 CH.sub.3                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 SCH.sub.3                                                                  OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                 OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    4-picolyl      OCH.sub.3                                                                         OCH.sub. 3                                                                             CH                      H  H          C.sub.2 H.sub.5                                                                           CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                OCH.sub.3                                                                         CH.sub.3 N                       H  H           -n-C.sub.5 H.sub.11                                                                      CH.sub.2 CH.sub.2 CH.sub.2 Cl                                                                OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.2 CH═CHCH.sub.3                                                                CHF.sub.2      OCH.sub.3                                                                         CH.sub.3 N                       H  H          cyclopropyl CHF.sub.2      OCH.sub.3                                                                         CH.sub.3 N                       H  H          cyclopropyl CHF.sub.2      OCH.sub.3                                                                         CH.sub.3 N                       H  H          4-CH.sub.3 -cyclohexyl                                                                    CHF.sub.2      OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.2 -cyclobutyl                                                                      CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         CH.sub.3 N                       H  H          1-cyclohexen-1-yl                                                                         CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.2 CH.sub.2 Cl                                                                      CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br                                                    CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 Br                                                    OCH.sub.3      OCH.sub.3                                                                         CH                               H  H          CH.sub.2 CF.sub.3                                                                         CHF.sub.2      OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CH.sub.3 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          OCH.sub.2 CH.sub.3                                                                        CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          OCH.sub.2 CH.sub.3                                                                        CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CH.sub.2 Br                                                                         Cl  OCH.sub.3                                                                              CH                      H  H          OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 -oxirane                                                                         CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 -oxirane                                                                         CH.sub.2 CH.sub.2 Br                                                                         OC.sub.2 H.sub.5                                                                  OCH.sub.3                                                                              CH                      H  H          CH.sub. 2 CH.sub.2 OC(O)N(CH.sub.3).sub.2                                                 CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         C.tbd.CH N                       H  H          CH.sub.2 CH.sub.2 OC(O)N(CH.sub.3).sub.2                                                  CH.sub.2 CH.sub.2 Br                                                                         Br  OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 SOCH.sub.3                                                              CH.sub.2 CH.sub.2 Br                                                                         CF.sub.3                                                                          CF.sub.3 CH                      H  H          CH.sub.2 CH.sub.2 SOCH.sub.3                                                              CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.2 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                       CH.sub.2 CH.sub.2 Br                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                       CH.sub.2 CH.sub.2 Br                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CF.sub.2 H  CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 F                                                                       CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 F                                                                       CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 CH.sub.2 Br                                                                      CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CH.sub.2 Br                                                                      CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          CH.sub.3 N                       H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.3    CN             OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          CH.sub.3    CN             OCH.sub.3                                                                         CH.sub.3 N                       H  H          CH.sub.3    CN             CH.sub.3                                                                          CH.sub.3 CH                      H  H          CH.sub.3    CN             CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CN             Cl  OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CN             OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  4-Cl       CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  5-Cl       CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-Cl       CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub. 3                                                                        OCH.sub.3                                                                              CH                      H  5-OCH.sub.3                                                                              CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-OCH.sub.3                                                                              CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-SCH.sub.3                                                                              CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-SO.sub.2 CH.sub.3                                                                      CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                    CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  6-SO.sub.2 NHCH.sub.3                                                                    CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  5-CN       CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      CH.sub.3                                                                         H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      CH.sub.3                                                                         H          CH.sub.3    CH.sub.2 CH.sub.2 Cl                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      CH.sub.3                                                                         H          CH.sub.3    CH.sub.2 -oxirane                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      CH.sub.3                                                                         H          CH.sub.2 C.tbd.CH                                                                         CH.sub.2 C.tbd.CH                                                                            OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      CH.sub.3                                                                         H          CH.sub.2 CF.sub.3                                                                         CH.sub. 2 CF.sub.3                                                                           OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    2-Pyridyl      OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    2-Pyridyl      CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          CH.sub.3    CH.sub.2 CH.sub.2 --                                                                         OCH.sub.3                                                                         OCH.sub.3                                                                              CH                                                Pyridin-2-yl                                        H  H          CH.sub.3    CH.sub.2 CH.sub.2 --                                                                         CH.sub.3                                                                          OCH.sub.3                                                                              N                                                 Pyridin-2-yl                                        H  H          CH.sub.3    Thiazol-2-yl   OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          CH.sub.3    Thiazol-2-yl   CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          --CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 --                                                     CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 --                                                     CH.sub.3                                                                          OCH.sub.3                                                                              N                       H  H          --CH.sub.2 CH.sub.2 CH.sub.2 CH(CH.sub.3)CH.sub.2 --                                                     OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH(Cl)CH(Cl)CH.sub.2 --                                                                       CH.sub.3                                                                          CH.sub.3 CH                      H  H          --CH.sub.2 CH(Cl)CH(Cl)CH.sub.2 --                                                                       CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH(Cl)CH(Cl)CH.sub.2 --                                                                       OCH.sub.3                                                                         OCH.sub.3                                                                              N                       H  H          --CH.sub. 2 CH(Cl)CH(Cl)CH.sub.2 --                                                                      Cl  OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                                          Cl  OCH.sub.3                                                                              CH 210-217(d)           H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                                          CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH 220-230(d)           H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                                          CH.sub.3                                                                          OCH.sub.2 CH.sub.2 CH.sub.3                                                            CH 193-196(d)           H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                                          CH.sub.3                                                                          OCH(CH.sub.3).sub.2                                                                    CH 173-179(d)           H  H          --CH.sub.2 CH(Br)CH(Br)CH.sub.2 --                                                                       CH.sub.3                                                                          OCH.sub.3                                                                              CH                      H  H          --CH.sub.2 CH(Br)CH(Br)CH.sub.2 --                                                                       OCH.sub.3                                                                         OCH.sub.3                                                                              CH                      H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          CH.sub.3 CH 175-176              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          OCH.sub.3                                                                              CH 170-171              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              CH 212-214              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          Cl  OCH.sub.3                                                                              CH 172-173              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          OCH.sub.3                                                                              N  177-178              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCH.sub.3                                                                         OCH.sub.3                                                                              N  182-184              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          CH.sub.3                                                                          CH.sub.3 N  178-179              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                                                          CH.sub.3 CH 152-153              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                                                          OCH.sub.3                                                                              CH 127-128              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 OCH.sub.3                                                                         OCH.sub.3                                                                              CH 188-189              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 Cl  OCH.sub.3                                                                              CH 155.5-156.5          H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                                                          OCH.sub.3                                                                              N  155-156              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 OCH.sub.3                                                                         OCH.sub.3                                                                              N  150-151              H  3-CH.sub.3 CH.sub.3    CH.sub.2 CH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                                                          CH.sub.3 N  146-148              H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCF.sub.2 H                                                                       H        CH                      H  H          CH.sub. 3   CH.sub.2 CH.sub.2 F                                                                          OCF.sub.2 H                                                                       CH.sub.3 CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCF.sub.2 H                                                                       OCH.sub.3                                                                              CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCF.sub.2 H                                                                       OCF.sub.2 H                                                                            CH                      H  H          CH.sub.3    CH.sub.2 CH.sub.2 F                                                                          OCF.sub.2 H                                                                       OC.sub.2 H.sub.5                                                                       CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCF.sub.2 H                                                                       N(CH.sub.3).sub.2                                                                      CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCF.sub.2 H                                                                       SCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCF.sub.2 H                                                                       Cl       CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCF.sub.2 H                                                                       OCH.sub.2 CH.sub.2 OCH.sub.3                                                           CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 CF.sub.3                                                                            OCF.sub.2 H                                                                       CH.sub.2 SCH.sub.3                                                                     CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       OCH.sub.3                                                                              CH                      H  H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       CH.sub.3 CH                      H  5-OCH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       CH.sub.3 CH                      H  6-OCH.sub.3                                                                              CH.sub. 2 CF.sub.3                                                                        CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       CH.sub.3 CH                      H  6-Cl       CH.sub.2 CF.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       CH.sub.3 CH                      CH.sub.3                                                                         H          CH.sub.2 CF.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                            OCF.sub.2 H                                                                       CH.sub.3 CH                      H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                           OCF.sub.2 H    CH.sub.3                                                                          CH       183-187(d)              H  H          --CH.sub.2 CH═CHCH.sub.2 --                                                           OCF.sub.2 H    OCH.sub.3                                                                         CH       212-215                 __________________________________________________________________________

                  TABLE IIIa                                                      ______________________________________                                        Formula III, W = S                                                                                                         m.p.                             R   R.sub. 1                                                                            R.sub. 3  R.sub. 4                                                                              X     Y     Z    (°C.)                     ______________________________________                                        H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           N                                     H   H     CF.sub.2 H                                                                              CH.sub.2 C.tbd.CH                                                                     OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 Cl                                                                  OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CF.sub.2 H                                                                              CH.sub.2 CH.sub.2 F                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           N                                     H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   Cl    OCH.sub.3                                                                           CH                                    H   H     CH.sub.2 CF.sub.3                                                                       CH.sub.2 CF.sub.3                                                                     OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.2 CH.sub.2 F                                                                     CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 Cl                                                                  OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           N                                     H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   CH.sub.3                                                                            OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    H   H     CH.sub.3  CH.sub.2 CH.sub.2 F                                                                   OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                    ______________________________________                                    

                                      TABLE IV                                    __________________________________________________________________________    Formula IV, W = 0                                                                                                        m.p.                               R  R.sub.1                                                                            R.sub.3                                                                             R.sub.4  A  X.sub.1                                                                            X.sub.2                                                                           Y Y.sub.1                                                                          Y.sub.2                                                                          (°C.)                       __________________________________________________________________________    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                    A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                    A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                    A-2                                                                              OCH.sub.2 F                                                                        --  --                                                                              O  --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 F                                                                    A-2                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              O  --                                    H  H    CH.sub.3                                                                            CH.sub.2 -oxirane                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  H    CH.sub.3                                                                            CH.sub.2 -oxirane                                                                      A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                    H  H    CH.sub.2 CF.sub.3                                                                   CF.sub.2 H                                                                             A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                    H  H    CH.sub.2 CF.sub.3                                                                   CF.sub.2 H                                                                             A-2                                                                              OCH.sub.2 F                                                                        --  --                                                                              O  --                                    H  H    CH.sub.2 CF.sub.3                                                                   CF.sub.2 H                                                                             A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              O  --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH                                                                      A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                    H  H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              CH.sub.3                                                                           --  --                                                                              O  --                                    H  H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  5-OCH.sub. 3                                                                       CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  6-CL CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              CH.sub.2                                                                         --                                    CH.sub.3                                                                         H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              CH.sub.3                                                                           --  --                                                                              CH.sub.2                                                                         --                                    CH.sub.3                                                                         H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-2                                                                              OCH.sub.3                                                                          --  --                                                                              O  --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-3                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-3                                                                              OCHF.sub.2                                                                         --  --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CH.sub.2 Br                                                                   A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CH.sub.2 Br                                                                   A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 CF.sub.3                                                                      A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 CF.sub.3                                                                      A-3                                                                              OC.sub.2 H.sub.5                                                                   --  --                                                                              -- --                                    H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH.sub.3                                                                A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    H  5-Br CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                    H  6-SCH.sub.3                                                                        CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    CH.sub.3                                                                         H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              OCH.sub.3                                                                          --  --                                                                              -- --                                    CH.sub. 3                                                                        H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-3                                                                              CH.sub.3                                                                           --  --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                     H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                     H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-4                                                                              OCH.sub.2 F                                                                        --  --                                                                              -- H                                     H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                              H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Br                                                                   A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- CH.sub.3                              H  H    CF.sub.2 H                                                                          CH.sub.2 CF.sub.3                                                                      A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                     H  H    CF.sub.2 H                                                                          CH.sub.2 CF.sub.3                                                                      A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                     H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH                                                                      A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                     H  H    CF.sub.2 H                                                                          CH.sub.2 C.tbd.CH                                                                      A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- CH.sub.3                              H  H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                     H  5-SCH.sub.3                                                                        CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- H                                     H  6-CH.sub.3                                                                         CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-4                                                                              OCH.sub.3                                                                          --  --                                                                              -- CH.sub.3                              CH.sub.3                                                                         H    CH.sub.2 C.tbd.CH                                                                   CH.sub.2 C.tbd.CH                                                                      A-4                                                                              CH.sub.3                                                                           --  --                                                                              -- H                                     H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-5                                                                              --   CH.sub.3                                                                          --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH.sub.2 Cl                                                                   A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH(OCH.sub.3).sub.2                                                           A-5                                                                              --   CH.sub.3                                                                          --                                                                              -- --                                    H  H    CH.sub.3                                                                            CH.sub.2 CH(OCH.sub.3).sub.2                                                           A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CF.sub.2 H                                                                             A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CF.sub.2 H                                                                             A-5                                                                              --   CH.sub.3                                                                          --                                                                              -- --                                    H  H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    H  6-Br CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    CH.sub.3                                                                         H    CH.sub.2 CF.sub.3                                                                   CH.sub.2 CF.sub.3                                                                      A-5                                                                              --   OCH.sub.3                                                                         --                                                                              -- --                                    __________________________________________________________________________

                                      TABLE IVa                                   __________________________________________________________________________    Formula IV, W = S                                                                                               m.p.                                        R R.sub.1                                                                         R.sub.3                                                                            R.sub.4                                                                             A  X.sub.1                                                                           X.sub.2                                                                           Y Y.sub.1                                                                          Y.sub.2                                                                          (° C.)                               __________________________________________________________________________    H H CH.sub.3                                                                           CH.sub.2 CH.sub.2 F                                                                 A-2                                                                              OCH.sub.3                                                                         --  --                                                                              O  --                                             H H CH.sub.3                                                                           CH.sub.2 CH.sub.2 F                                                                 A-2                                                                              OCH.sub.3                                                                         --  --                                                                              CH.sub.2                                                                         --                                             H H CF.sub.2 H                                                                         CH.sub.2 CH.sub.2 F                                                                 A-3                                                                              CH.sub.3                                                                          --  --                                                                              -- --                                             H H CH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl                                                                A-3                                                                              OCH.sub.3                                                                         --  --                                                                              -- --                                             H H CH.sub.3                                                                           CH.sub.2 CH.sub.2 Br                                                                A-4                                                                              CH.sub.3                                                                          --  --                                                                              -- CH.sub.3                                       H H CH.sub.2 CF.sub.3                                                                  CH.sub.2 CF.sub.3                                                                   A-4                                                                              OCH.sub.3                                                                         --  --                                                                              -- H                                              H H CH.sub.3                                                                           CH.sub.2 CH.sub.2 F                                                                 A-5                                                                              --  OCH.sub.3                                                                         --                                                                              -- --                                             H H CHF.sub.2                                                                          CH.sub.2 CF.sub.3                                                                   A-5                                                                              --  OCH.sub.3                                                                         --                                                                              -- --                                             __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE V                                                         ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent (s)                                                                             Surfactant (s)                                  ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95       5-99.9 0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, New Jersey, but other solids, either mined or manufactured,may be used. The more absorptive diluents are preferred for wettablepowders and the denser ones for dusts. Typical liquid diluents andsolvents are described in Marsden, "Solvents Guide," 2nd Ed.,Interscience, New York, 1950. Solubility under 0.1% is preferred forsuspension concentrates; solution concentrates are preferably stableagainst phase separation at 0° C. "McCutcheon's Detergents andEmulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as wellas Sisely and Wood, "Encyclopedia of Surface Active Agents", ChemicalPublishing Co., Inc., New York, 1964, list surfactants and recommendeduses. All formulations can contain minor amounts of additives to reducefoaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 3

Wettable Powder

    ______________________________________                                        N-Cyclopropyl-N'-8 (4,6-dimethoxypyrimidin-2-yl)amino-                        carbonyl]-1,2-benzenedisulfonamide                                                                  50%                                                     sodium alkylnaphthalenesulfonate                                                                     2%                                                     low viscosity methyl cellulose                                                                       2%                                                     diatomaceous earth    46%                                                     ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 4

Granule

    ______________________________________                                        Wettable Powder of Example 3                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh: 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 5

Extruded Pellet

    ______________________________________                                        N-Cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-                        yl)aminocarbonyl]-1,2-benzenedisulfonamide                                                              25%                                                 anhydrous sodium sulfate  10%                                                 crude calcium ligninsulfonate                                                                            5%                                                 sodium alkylnaphthalenesulfonate                                                                         1%                                                 calcium/magnesium bentonite                                                                             59%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 6

Low Strength Granule

    ______________________________________                                        N-Cyclopropyl-N'-[(4,6-dimethoxypyrimidin-2-yl)amino-                         carbonyl]-1,2-benzenedisulfonamide                                                                   1%                                                     N,N-dimethylformamide  9%                                                     attapulgite granules  90%                                                     (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 7

Aqueous Suspension

    ______________________________________                                        N-Cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-                        yl)aminocarbonyl]-1,2-benzenedisulfonamide                                                              40%                                                 polyacrylic acid thickener                                                                             0.3%                                                 dodecylphenol polyethylene glycol ether                                                                0.5%                                                 disodium phosphate         1%                                                 monosodium phosphate     0.5%                                                 polyvinyl alcohol        1.0%                                                 water                    56.7%                                                ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 8

Oil Suspension

    ______________________________________                                        N-Cyclopropyl-N'-[(4,6-dimethoxypyrimidin-2-yl)amino-                         carbonyl]-1,2-benzenedisulfonamide                                                                  35%                                                     blend of polyalcohol carboxylic                                                                      6%                                                     esters and oil soluble petroleum                                              sulfonates                                                                    xylene                59%                                                     ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 9

Granule

    ______________________________________                                        N-Cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-                        yl)aminocarbonyl]-1,2-benzenedisulfonamide                                                              80%                                                 wetting agent              1%                                                 crude ligninsulfonate salt (containing                                                                  10%                                                 5-20% of the natural sugars)                                                  attapulgite clay           9%                                                 ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 10

High Strength Concentrate

    ______________________________________                                        N-Cyclopropyl-N'-[(4,6-dimethoxypyrimidin-2-yl)amino-                         carbonyl]-1,2-benzenedisulfonamide                                                                   99%                                                    silica aerogel        0.5%                                                    synthetic amorphous silica                                                                          0.5%                                                    ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 11

Wettable Powder

    ______________________________________                                        N-Cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-                        yl)aminocarbonyl]-1,2-benzenedisulfonamide                                                               90%                                                dioctyl sodium sulfosuccinate                                                                           0.1%                                                synthetic fine silica     9.9%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 12

Wettable Powder

    ______________________________________                                        N-Cyclopropyl-N'-[(4.6-dimethoxypyrimidin-2-yl)amino-                         carbonyl]-1,2-benzenedisulfonamide                                                                  40%                                                     sodium ligninsulfonate                                                                              20%                                                     montmorillonite clay  40%                                                     ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 13

Dust

    ______________________________________                                        N-Cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-                        yl)aminocarbonyl]-1,2-benzenedisulfonamide                                                              10%                                                 attapulgite               10%                                                 Pyrophyllite              80%                                                 ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention arehighly active preemergent or postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpostemergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Some of thecompounds have utility for selective weed control in crops such aswheat. Alternatively, the subject compounds are useful to modify plantgrowth.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.01 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for plant growth modificationor for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide; examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), cheatgrass (Bromus secalinus),velvetleaf (Abutilon theophrasti), morningglory (Ipomoea spp.),cocklebur (Xanthium Pensylvanicum), sorghum, corn, soybean, sugar beet,cotton, rice, wheat and purple nutsedge (Cyperus rotundus) tubers wereplanted and treated preemergence with the test chemicals dissolved in anon-phytotoxic solvent. At the same time, these crop and weed specieswere treated with a soil/foliage application. At the time of treatment,the plants ranged in height from 2 to 18 cm. Treated plants and controlswere maintained in a greenhouse for sixteen days, after which allspecies were compared to controls and visually rated for response totreatment. The ratings, summarized in Table A, are based on a numericalscale extending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings:

B=burn:

C=chlorosis/necrosis:

D=defoliation:

E=emergence inhibition:

G=growth retardation:

H=formative effect:

U=unusual pigmentation:

X=axillary stimulation:

S=albinism; and

6Y=abscised buds or flowers.

    __________________________________________________________________________    Compounds                                                                     __________________________________________________________________________     ##STR29##                                                                    Compound  R.sub.2     X       Y      Z                                        __________________________________________________________________________    1         CH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                              CH.sub.3                                                                             CH                                       2         CH.sub.2 C.sub.6 H.sub.5                                                                  OCH.sub.3                                                                             CH.sub.3                                                                             CH                                       3         CH.sub.2 C.sub.6 H.sub.5                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       4         CH.sub.2 C.sub.6 H.sub.5                                                                  Cl      OCH.sub.3                                                                            CH                                       5         CH.sub.2 C.sub.6 H.sub.5                                                                  OCH.sub.3                                                                             CH.sub.3                                                                             N                                        6         CH.sub.2 C.sub.6 H.sub.5                                                                  OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        7         cyclopropyl CH.sub.3                                                                              CH.sub.3                                                                             CH                                       8         cyclopropyl CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       9         cyclopropyl OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       10        cyclopropyl Cl      OCH.sub.3                                                                            CH                                       11        cyclopropyl OCH.sub.3                                                                             CH.sub.3                                                                             N                                        12        cyclopropyl OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        13        cyclobutyl  CH.sub.3                                                                              CH.sub.3                                                                             CH                                       14        cyclobutyl  CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       15        cyclobutyl  OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       16        cyclobutyl  Cl      OCH.sub.3                                                                            CH                                       17        cyclobutyl  OCH.sub.3                                                                             CH.sub.3                                                                             N                                        18        cyclobutyl  OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        19        OCH.sub.3   CH.sub.3                                                                              CH.sub.3                                                                             CH                                       20        OCH.sub.3   CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       21        OCH.sub.3   OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       22        OCH.sub.3   Cl      OCH.sub.3                                                                            CH                                       23        OCH.sub.3   CH.sub.3                                                                              OCH.sub.3                                                                            N                                        24        OCH.sub.3   OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        25        CH.sub.2 CH(OCH.sub.3).sub.2                                                              CH.sub.3                                                                              CH.sub.3                                                                             CH                                       26        CH.sub.2 CH(OCH.sub.3).sub.2                                                              CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       27        CH.sub.2 CH(OCH.sub.3).sub.2                                                              OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       28        CH.sub.2 CH(OCH.sub.3).sub.2                                                              Cl      OCH.sub.3                                                                            CH                                       29        CH.sub.2 CH(OCH.sub.3).sub.2                                                              CH.sub.3                                                                              OCH.sub.3                                                                            N                                        30        CH.sub.2 CH(OCH.sub.3).sub.2                                                              OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        31        CH.sub.2 CCH                                                                              CH.sub.3                                                                              CH.sub.3                                                                             CH                                       32        CH.sub.2 CCH                                                                              CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       33        CH.sub.2 CCH                                                                              OCH.sub.3                                                                             OCH.sub. 3                                                                           CH                                       34        CH.sub.2 CCH                                                                              Cl      OCH.sub.3                                                                            CH                                       35        CH.sub.2 CCH                                                                              CH.sub.3                                                                              OCH.sub.3                                                                            N                                        36        CH.sub.2 CCH                                                                              OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        37        CH.sub.2 CH.sub.2 F                                                                       CH.sub.3                                                                              CH.sub.3                                                                             CH                                       38        CH.sub.2 CH.sub.2 F                                                                       OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       39        CH.sub.2 CH.sub.2 F                                                                       Cl      OCH.sub.3                                                                            CH                                       40        CH.sub.2 CH.sub.2 F                                                                       CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       41        CH.sub.2 CH.sub.2 F                                                                       CH.sub.3                                                                              OCH.sub.3                                                                            N                                        42        CH.sub.2 CH.sub.2 F                                                                       OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        43        cyclopentyl CH.sub.3                                                                              CH.sub.3                                                                             CH                                       44        cyclopentyl CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       45        cyclopentyl OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       46        cyclopentyl Cl      OCH.sub.3                                                                            CH                                       47        cyclopentyl CH.sub.3                                                                              OCH.sub.3                                                                            N                                        48        cyclopentyl OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        49        CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                              CH.sub.3                                                                             CH                                       50        CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       51        CH.sub.2 CH.sub.2 OH                                                                      OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       52        CH.sub.2 CH.sub.2 OH                                                                      Cl      OCH.sub.3                                                                            CH                                       53        CH.sub.2 CH.sub.2 OH                                                                      CH.sub.3                                                                              OCH.sub.3                                                                            N                                        54        CH.sub.2 CH.sub.2 OH                                                                      OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        55        CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2                                                       CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       56                                                                                       ##STR30##  OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       57        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             CH.sub.3                                                                              CH.sub.3                                                                             CH                                       58        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       59        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       60        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       61        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        62        CH.sub.2 CH.sub.2 CH.sub.2 Br                                                             Cl      OCH.sub.3                                                                            N                                        63        CH.sub.2 -cyclopropyl                                                                     CH.sub.3                                                                              CH.sub.3                                                                             CH                                       64        CH.sub.2 -cyclopropyl                                                                     CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       65        ch.sub.2 -cyclopropyl                                                                     OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       66        CH.sub.2 -cyclopropyl                                                                     CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       67        CH.sub.2 -cyclopropyl                                                                     OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        68        CH.sub.2 -cyclopropyl                                                                     Cl      OCH.sub.3                                                                            N                                        69        CH.sub.2 CF.sub.2 CF.sub. 3                                                               CH.sub.3                                                                              CH.sub.3                                                                             CH                                       70        CH.sub.2 CF.sub.2 CF.sub.3                                                                CH.sub.3                                                                              OCH.sub.3                                                                            CH                                       71        CH.sub.2 CF.sub.2 CF.sub.3                                                                OCH.sub.3                                                                             OCH.sub.3                                                                            CH                                       72        CH.sub.2 CF.sub.2 CF.sub.3                                                                CH.sub.3                                                                              OCH.sub.3                                                                            N                                        73        CH.sub.2 CF.sub.2 CF.sub.3                                                                OCH.sub.3                                                                             OCH.sub.3                                                                            N                                        __________________________________________________________________________     ##STR31##                                                                    Compound                                                                            R.sub.1                                                                           R.sub.2                                                                          R.sub.3  X    Y       Z  m.p. (°C.)                       __________________________________________________________________________    74    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                    CH.sub.3                                                                           CH.sub.3                                                                              CH 175 to 176                              75    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                    CH.sub.3                                                                           OCH.sub.3                                                                             CH 170 to 171                              76    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                    OCH.sub.3                                                                          OCH.sub.3                                                                             CH 212 to 214                              77    3-CH.sub.3                                                                        CH.sub. 3                                                                        CH.sub.2 CH.sub.2 F                                                                    Cl   OCH.sub.3                                                                             CH 172 to 173                              78    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                    CH.sub.3                                                                           OCH.sub.3                                                                             N  177 to 178                              79    3-CH.sub.3                                                                        CH.sub.2 CH.sub.2 F                                                              OCH.sub.3                                                                              OCH.sub.3                                                                          N       182 to 184                                 80    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 F                                                                    CH.sub.3                                                                           CH.sub.3                                                                              N  178 to 179                              81    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           CH.sub.3                                                                           CH.sub.3                                                                              CH 152 to 153                              82    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           CH.sub.3                                                                           OCH.sub.3                                                                             CH 127 to 128                              83    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           OCH.sub.3                                                                          OCH.sub.3                                                                             CH 188 to 189                              84    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           Cl   OCH.sub.3                                                                             CH 155.5 to 156.5                          85    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           CH.sub.3                                                                           OCH.sub.3                                                                             N  155 to 156                              86    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           OCH.sub.3                                                                          OCH.sub.3                                                                             N  150 to 151                              87    3-CH.sub.3                                                                        CH.sub.3                                                                         CH.sub.2 CH.sub.2 CH.sub.2 F                                                           CH.sub.3                                                                           CH.sub.3                                                                              N  146 to 148                              88    H   CH.sub.2 CHCHCH.sub.2                                                                     Cl   OCH.sub.3                                                                             CH 210 to 217(d)                           89    H   CH.sub.2 CHCHCH.sub.2                                                                     OCH.sub.3                                                                          OCH.sub.3                                                                             CH 220 to 230(d)                           90    H   CH.sub.2 CHCHCH.sub.2                                                                     CH.sub.3                                                                           OCH.sub.2 CH.sub.2 CH.sub.3                                                           CH 193 to 196(d)                           91    H   CH.sub.2 CHCHCH.sub.2                                                                     CH.sub.3                                                                           OCH(CH.sub.3).sub.2                                                                   CH 173 to 179                              92    H   CH.sub.2 CHCHCH.sub.2                                                                     OCF.sub.2 H                                                                        CH.sub.3                                                                              CH 183 to 187(d)                           93    H   CH.sub.2 CHCHCH.sub.2                                                                     OCF.sub.2 H                                                                        OCH.sub.3                                                                             CH 212 to 215                              __________________________________________________________________________

                  TABLE A                                                         ______________________________________                                                  Cmpd. 1  Cmpd. 2   Cmpd. 3 Cmpd. 4                                  Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        4C,9G     9C      4C,9G                                    Cocklebur 4C,9G    5C,9G     10C     5C,9G                                    Velvetleaf                                                                              4C,8H    9C        9C      4C,8H                                    Nutsedge  2G       3C,8G     3C,9G   3C,8G                                    Crabgrass 0        3G        2C,8G   2G                                       Barnyardgrass                                                                           5H       2C,7H     9C      3C,7H                                    Cheatgrass                                                                              2C,7G    9C        5C,9G   6G                                       Wild Oats 6G       6G        8G      0                                        Wheat     3G       2G        6G      0                                        Corn      2C,5H    2C,8G     2U,9G   2G                                       Soybean   4C,8H    9C        9C      3C,7G                                    Rice      5C,9G    6C,9G     6C,9G   3C,8G                                    Sorghum   2C,8H    3C,9H     9C      4C,9H                                    Sugar beet                                                                              9C       4C,8G     9C      4C,8H                                    Cotton    4C,9H    4C,9G     5C,9G   4C,9H                                    PREEMERGENCE                                                                  Morninglory                                                                             6G       6G        9G      6G                                       Cocklebur 5H       8H        8H      0                                        Velvetleaf                                                                              6H       4C,9G     5C,9G   5G                                       Nutsedge  0        6G        10E     5G                                       Crabgrass 2G       2G        5G      2G                                       Barnyardgrass                                                                           0        3C,8H     3C,9H   3H                                       Cheatgrass                                                                              8G       5C,9H     4C,8H   6G                                       Wild Oats 2C,6G    2C,9G     3C,9H   3G                                       Wheat     6G       8G        2C,9G   3G                                       Corn      6G       2C,9G     9G      3C,6G                                    Soybean   0        3C,7G     3C,6G   0                                        Rice      9H       10E       10E     9H                                       Sorghum   4C,5G    4C,9H     9H      2C,9G                                    Sugar beet                                                                              4C,8G    5c,9G     9G      8G                                       Cotton    4G       7G        8G      4G                                       ______________________________________                                                  Cmpd. 5  Cmpd. 6   Cmpd. 7 Cmpd. 8                                  Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            4C,8G    4C,8H     5C,9G   10C                                      Cocklebur 3C,5G    0         9C      10C                                      Velvetleaf                                                                              5C,9G    4C,8H     9C      9C                                       Nutsedge  0        0         8G      2C,7G                                    Crabgrass 2G       0         4G      4G                                       Barnyardgrass                                                                           3C,9H    3C,6H     3C,9H   3C,8H                                    Cheatgrass                                                                              4C,9G    2C,7G     3C,8G   4C,8G                                    Wild Oats 5C,9G    5C,9H     8G      2C,5G                                    Wheat     4C,9G    2G        5G      2G                                       Corn      5U,9C    3C,9H     7H      4C,9H                                    Soybean   9C       5C,9G     9C      9C                                       Rice      6C,9G    6C,9G     5C,9G   5C,9G                                    Sorghum   3C,8H    3C,6H     3U,9H   2C,8G                                    Sugar beet                                                                              9C       5C,9H     3C,6G   5C,9G                                    Cotton    5C,9G    5C,9G     9C      5C,9G                                    PREEMERGENCE                                                                  Morningglory                                                                            7G       4G        9G      8G                                       Cocklebur 4G       0         8H      8H                                       Velvetleaf                                                                              2C,8G    3C,8H     4C,9G   9G                                       Nutsedge  0        0         7G      10E                                      Crabgrass 0        0         5G      8G                                       Barnyardgrass                                                                           3H       0         6G      4C,9H                                    Cheatgrass                                                                              3C,8H    2G        7G      9H                                       Wild Oats 3C,8G    0         8G      3C,7G                                    Wheat     2C,8G    0         8G      7G                                       Corn      8G       3C,7G     8G      2C,9G                                    Soybean   3C,3G    2C        5H      3C,6H                                    Rice      9H       4C,8H     10E     5C,9H                                    Sorghum   3C,9H    4C,6H     10E     3C,9H                                    Sugar beet                                                                              9G       5C,9G     6G      8G                                       Cotton    7G       7G        8G      9G                                       ______________________________________                                                  Cmpd. 9  Cmpd. 10  Cmpd. 11                                                                              Cmpd. 11                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            9C       9C        10C     9C                                       Cocklebur 10C      9C        10C     10C                                      Velvetleaf                                                                              9C       2C,8G     9C      5C,9G                                    Nutsedge  5C,9G    2C,7G     3G      4G                                       Crabgrass 7G       4G        7G      6G                                       Barnyardgrass                                                                           5C,9G    3C,9H     5C,9H   3C,7H                                    Cheatgrass                                                                              5C,9G    8G        5C,9G   3C,8G                                    Wild Oats 3C,7G    0         5C,9G   4C,8G                                    Wheat     0        0         2C,9G   5G                                       Corn      4U,8H    3H        10C     10C                                      Soybean   5C,9G    3C,8G     9C      9C                                       Rice      4C,9G    7G        5C,9G   5C,9G                                    Sorghum   4U,9H    3U,9G     5U,9C   6C,9H                                    Sugar beet                                                                              9C       3C,6H     9C      9C                                       Cotton    4C,9H    5C,9H     5C,9G   5C,9H                                    PREEMERGENCE                                                                  Morningglory                                                                            9G       9G        9G      9G                                       Cocklebur --       4C,5H     9H      --                                       Velvetleaf                                                                              5C,9G    3G        5C,9G   5C,9G                                    Nutsedge  10E      10E       3G      4G                                       Crabgrass 5C,9G    5G        7G      8G                                       Barnyardgrass                                                                           9H       3C,7H     3C,8H   3C,8H                                    Cheatgrass                                                                              9H       5G        2C,7H   2C,5G                                    Wild Oats 3C,6G    2G        3C,8H   2C,6G                                    Wheat     3G       0         2C,8G   3C,8G                                    Corn      9G       2C,5G     5C,9G   3C,9G                                    Soybean   5H       0         4C,6H   3C,6H                                    Rice      10E      3C,8H     10E     5C,9H                                    Sorghum   2C,9G    3C,8H     10E     5C,9H                                    Sugar beet                                                                              9G       7G        5C,9G   5C,9G                                    Cotton    9G       8G        9G      8G                                       ______________________________________                                                  Cmpd. 13 Cmpd. 14  Cmpd. 15                                                                              Cmpd. 16                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            2H       4C,9G     9C      4C,8H                                    Cocklebur 4C,9G    9C        9C      5C,9G                                    Velvetleaf                                                                              4C,8H    4C,8H     5C,9G   4G                                       Nutsedge  5G       3C,8G     7G      7G                                       Crabgrass 0        4G        6G      2G                                       Barnyardgrass                                                                           2H       3C,8H     3C,9H   2C,8H                                    Cheatgrass                                                                              3C,8G    4C,8G     4C,8G   5G                                       Wild Oats 8G       7G        8G      2G                                       Wheat     0        0         5G      0                                        Corn      3C,6H    4U,9G     4C,9G   6H                                       Soybean   3C,8G    9C        5C,9G   2C,5H                                    Rice      5C,9G    5C,9G     5C,9G   8G                                       Sorghum   3C,7H    4C,9H     4C,9H   2C,9H                                    Sugar beet                                                                              4C,8H    9C        5C,9G   2C,3G                                    Cotton    4C,7H    4C,7G     4C,9G   4C,8G                                    PREEMERGENCE                                                                  Morningglory                                                                            5G       8G        9G      7G                                       Cocklebur 4G       7H        8H      1C                                       Velvetleaf                                                                              0        8G        9G      0                                        Nutsedge  0        8G        10E     0                                        Crabgrass 4G       4G        3G      3G                                       Barnyardgrass                                                                           0        8G        9H      2G                                       Cheatgrass                                                                              6G       9H        10E     5G                                       Wild Oats 2C,5G    4C,7H     2C,8H   3G                                       Wheat     4G       8G        8H      0                                        Corn      2C,5G    4C,9H     9G      2C,5G                                    Soybean   1H       4C,6H     3C,6H   0                                        Rice      8H       9H        10E     3C,8H                                    Sorghum   3C,7G    5C,9H     4C,9H   3C,9H                                    Sugar beet                                                                              8G       5C,9G     9G      8G                                       Cotton    3G       9G        9G      0                                        ______________________________________                                                  Cmpd. 17 Cmpd. 18  Cmpd. 19                                                                              Cmpd. 20                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                             9C      5C,9G     10C     6C,9G                                    Cocklebur 3C,9G    5G        9C      9C                                       Velvetleaf                                                                              5C,9G    3C,7G     9C      9C                                       Nutsedge  0        4G        4C,9G   4C,9G                                    Crabgrass 3G       2G        6G      4C,8G                                    Barnyardgrass                                                                           4C,9H    3C,7H     3C,8H   4C,8H                                    Cheatgrass                                                                              2C,7G    5G        2C,8G   9C                                       Wild Oats 4G       8G        5G      3G                                       Wheat     4G       7G        4G      5G                                       Corn      5C,9G    3U,9G     7H      8H                                       Soybean   9C       5C,9G     4C,8G   9C                                       Rice      5C,9G    9G        5C,9G   9C                                       Sorghum   3U,9G    5C,9G     3C,8G   8H                                       Sugar beet                                                                              9C       3C,7G     5C,9G   5C,9G                                    Cotton    4C,9G    4C,7G     9C      9C                                       PREEMERGENCE                                                                  Morningglory                                                                            9G       7H        9H      9G                                       Cocklebur 5H       1C        9H      --                                       Velvetleaf                                                                              2G       0         5C,9G   5C,9G                                    Nutsedge  0        0         8G      9G                                       Crabgrass 5G       2G        4C,8G   7G                                       Barnyardgrass                                                                           2G       0         3C,8H   3C,8H                                    Cheatgrass                                                                              5G       0         3C,9H   9H                                       Wild Oats 2H       0         4C,8G   2C,8G                                    Wheat     6G       3G        6C,9H   3C,8H                                    Corn      8G       3C,7G     3U,9H   5U,9H                                    Soybean   2C,5H    1C        7H      8H                                       Rice      7H       5G        10H     10E                                      Sorghum   4C,9H    3C,5G     9H      9H                                       Sugar beet                                                                              4C,8G    8G        10C     10E                                      Cotton    7G       3G        8G      9G                                       ______________________________________                                                  Cmpd. 21 Cmpd. 22  Cmpd. 23                                                                              Cmpd. 24                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            10C      10C       10C     10C                                      Cocklebur 10C      9C        9C      4G                                       Velvetleaf                                                                              9C       5C,9G     9C      9C                                       Nutsedge  6C,9G    5C,9G     4G      3G                                       Crabgrass 3C,5G    2C,5G     5C,9G   3C,8G                                    Barnyardgrass                                                                           9C       4C,7H     5C,9H   6C,9H                                    Cheatgrass                                                                              9C       6G        3C,6G   5G                                       Wild Oats 3C,7G    0         6C,9G   5C,9G                                    Wheat     4G       0         5C,9G   2C,7G                                    Corn      6C,9H    6H        9C      10C                                      Soybean   9C       5C,9G     9C      9C                                       Rice      6C,9G    4C,7G     9C      9C                                       Sorghum   9C       4C,8H     9C      6C,9H                                    Sugar beet                                                                              10C      3C,6G     10C     9C                                       Cotton    10C      9C        10C     9C                                       PREEMERGENCE                                                                  Morningglory                                                                            9G       8G        9G      9G                                       Cocklebur 8H       9H        9H      8H                                       Velvetleaf                                                                              5C,9G    8G        9C      3C,7G                                    Nutsedge  10E      10E       5G      0                                        Crabgrass 3C,7G    0         3C,7G   2C,5G                                    Barnyardgrass                                                                           8H       4C,4H     3C,8H   3C,7H                                    Cheatgrass                                                                              9H       2C,5G     3C,7H   3C,6G                                    Wild Oats 3C,6G    2C,4G     5C,9H   3C,8G                                    Wheat     5G       2G        4C,9H   4C,9G                                    Corn      5U,9G    3C,8G     3C,9H   5C,9H                                    Soybean   8H       2H        8H      4C,8H                                    Rice      10E      9H        10E     10E                                      Sorghum   5C,9H    3C,8G     10E     5C,9H                                    Sugar beet                                                                              9G       3C,8G     10C     5C,9G                                    Cotton    9G       8G        4C,9G   5C,9G                                    ______________________________________                                                  Cmpd. 25 Cmpd. 26  Cmpd. 27                                                                              Cmpd. 28                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            2C,7G    3C,8G     3C,9H   2C,4G                                    Cocklebur 3C,9H    3C,9H     5C,9G   8H                                       Velvetleaf                                                                              6H       3C,8G     9C      1H                                       Nutsedge  2G       4G        2C,9G   0                                        Crabgrass 3G       2G        3C,7G   2G                                       Barnyardgrass                                                                           3C,9H    3C,9H     9H      3C,9H                                    Cheatgrass                                                                              2C,7G    3C,6G     3C,8G   3G                                       Wild Oats 2C,4G    2C,8G     7G      0                                        Wheat     0        0         4G      0                                        Corn      4G       2C,8H     3C,9H   5G                                       Soybean   2C,9G    5C,9G     5C,9G   5H                                       Rice      4C,9G    4C,9G     6C,9G   4C,9G                                    Sorghum   4C,8H    4C,9H     9H      4C,8H                                    Sugar beet                                                                              3C,7H    3C,6G     3C,9G   2G                                       Cotton    2C,5G    2C,5G     4C,9G   2G                                       PREEMERGENCE                                                                  Morningglory                                                                            2C,4G    7G        3C,5G   2C,9G                                    Cocklebur 2C       10C       8H      2H                                       Velvetleaf                                                                              3G       8G        5C,9G   2G                                       Nutsedge  0        4G        8G      0                                        Crabgrass 0        0         4G      0                                        Barnyardgrass                                                                           0        3C,8H     4C,9H   3C,7H                                    Cheatgrass                                                                              2G       8G        8G      4G                                       Wild Oats 2C,5G    3C,7G     2C,8G   3C,3G                                    Wheat     0        2C,5G     3C,9G   2G                                       Corn      2C,5G    3C,8H     4C,9G   2C,5G                                    Soybean   2C,2H    6G        3C,3H   3C,3G                                    Rice      3C,8H    3C,8H     4C,9H   8H                                       Sorghum   3C,7H    3C,8H     4C,9H   3C,8G                                    Sugar beet                                                                              2C,5G    2C,8G     6G      2G                                       Cotton    0        7G        3C,5G   3G                                       ______________________________________                                                  Cmpd. 29 Cmpd. 30  Cmpd. 31                                                                              Cmpd. 32                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            3C,8G    2C,5G     10C     10C                                      Cocklebur 2G       0         9C      9C                                       Velvetleaf                                                                              2G       0         10C     10C                                      Nutsedge  0        0         7G      2C,8G                                    Crabgrass 2G       0         6G      3C,7H                                    Barnyardgrass                                                                           4H       0         3C,8H   9H                                       Cheatgrass                                                                              0        0         3C,9G   5C,9G                                    Wild Oats 0        0         3C,8H   4C,8G                                    Wheat     0        0         3G      0                                        Corn      5H       5H        2H      9H                                       Soybean   3C,9G    2C,8H     2C,5G   5C,9G                                    Rice      2C,8G    5G        5C,9G   5C,9G                                    Sorghum   2H       2G        4C,9H   2C,9H                                    Sugar beet                                                                              3C,7G    2C,5G     9C      9C                                       Cotton    1H       2C,6H     4C,8G   9C                                       PREEMERGENCE                                                                  Morningglory                                                                            2C,4G    2C,4G     9H      9G                                       Cocklebur 5G       2H        9H      9H                                       Velvetleaf                                                                              5G       2G        9G      9C                                       Nutsedge  0        0         4G      7G                                       Crabgrass 2G       3G        3G      5G                                       Barnyardgrass                                                                           0        1C        3C,6G   2C,8H                                    Cheatgrass                                                                              0        0         8H      10E                                      Wild Oats 0        2C        2C,8G   5C,9G                                    Wheat     0        2G        7G      8G                                       Corn      2G       0         2C,7G   9H                                       Soybean   0        1C        2C,3G   3C,7H                                    Rice      3G       0         9H      10E                                      Sorghum   2C,4G    0         3C,9G   10H                                      Sugar beet                                                                              0        7G        8G      9C                                       Cotton    0        2G        9C      9C                                       ______________________________________                                                  Cmpd. 33 Cmpd. 34  Cmpd. 35                                                                              Cmpd. 36                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            10C      10C       10C     10C                                      Cocklebur 9C       9C        10C     8G                                       Velvetleaf                                                                              10C      10C       10C     9C                                       Nutsedge  2C,9G    9G        4G      5G                                       Crabgrass 3C,8G    6G        4C,8G   4C,8G                                    Barnyardgrass                                                                           5C,9H    4C,9H     9C      3C,5H                                    Cheatgrass                                                                              9C       2C,9G     9C      8G                                       Wild Oats 4C,9G    0         9C      5C,8G                                    Wheat     3G       0         5C,9G   8G                                       Corn      2C,9G    5H        9C      4U,9G                                    Soybean   9C       3C,8G     5C,9G   5C,9G                                    Rice      6C,9G    5C,9G     9C      9C                                       Sorghum   3C,9G    4C,9H     4U,9H   3C,9H                                    Sugar beet                                                                              9C       3C,8G     9C      9C                                       Cotton    9C       9C        9C      4C,9H                                    PREEMERGENCE                                                                  Morningglory                                                                            3C,9H    9G        9H      9G                                       Cocklebur 9H       8H        9H      8G                                       Velvetleaf                                                                              9G       9C        9C      9C                                       Nutsedge  10E      3C,9G     0       0                                        Crabgrass 7G       4G        2C,4G   4G                                       Barnyardgrass                                                                           9H       3C,7H     3C,8H   2C,3G                                    Cheatgrass                                                                              10H      2C,8G     3C,7G   3G                                       Wild Oats 3C,8G    2C,5G     3C,6G   2C,3G                                    Wheat     2C,8G    0         3C,8G   3C,6G                                    Corn      2U,9H    3C,7G     3C,9H   3C,9G                                    Soybean   9H       2C,2H     2C,3G   3C,3H                                    Rice      10E      5C,9H     9H      5C,9H                                    Sorghum   5C,9H    3C,9G     5C,9H   4C,9H                                    Sugar beet                                                                              9G       4C,8G     9C      9C                                       Cotton    9G       9G        9G      9G                                       ______________________________________                                                    Cmpd. 37     Cmpd. 38 Cmpd. 39                                    Rate kg/ha  0.05         0.05     0.05                                        ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                              9C           10C      10C                                         Cocklebur   9C           10C      10C                                         Velvetleaf  10C          10C      9C                                          Nutsedge    2C,9G        3C,9G    5C,9G                                       Crabgrass   6G           7G       4G                                          Barnyardgrass                                                                             9H           9C       9H                                          Cheatgrass  4C,9G        9C       2C,9G                                       Wild Oats   5C,9H        4C,8G    0                                           Wheat       3G           2G       0                                           Corn        8H           10C      7H                                          Soybean     4C,9G        9C       3C,8G                                       Rice        9C           9C       5C,9G                                       Sorghum     2C,9H        5C,9G    5C,9H                                       Sugar beet  4C,8G        9C       3C,7H                                       Cotton      9C           10C      4C,9G                                       PREEMERGENCE                                                                  Morningglory                                                                              9G           9G       9G                                          Cocklebur   9H           9H       9H                                          Velvetleaf  4C,9G        9C       9C                                          Nutsedge    6G           10E      10E                                         Crabgrass   4G           4G       0                                           Barnyardgrass                                                                             4G           5C,9H    4C,8H                                       Cheatgrass  8H           9H       8H                                          Wild Oats   2C,8G        5C,9G    2C,5G                                       Wheat       2C,5G        2C,9G    0                                           Corn        4C,8G        3U,9G    3C,7G                                       Soybean     3C,5H        9H       3C,3H                                       Rice        10E          10E      4C,9H                                       Sorghum     9H           9H       4C,9H                                       Sugar beet  4C,8G        9G       9G                                          Cotton      9G           9G       9G                                          ______________________________________                                                  Compound 40   Cmpd. 41                                              Rate kg/ha  0.05        0.01    0.05                                          ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                              10C         10C     10C                                           Cocklebur   10C         9C      10C                                           Velvetleaf  10C         10C     9C                                            Nutsedge    3C,9G       2C,8G   8G                                            Crabgrass   5G          2G      2C,6G                                         Barnyardgrass                                                                             9H          4C,8H   5C,9H                                         Cheatgrass  9C          5C,9G   4C,9G                                         Wild Oats   3C,9G       4C,9G   4C,9G                                         Wheat       5G          3G      2C,9G                                         Corn        2C,9H       2C,9H   5U,9G                                         Soybean     9C          9C      5C,9G                                         Rice        9C          5C,9G   5C,9G                                         Sorghum     3C,9G       3C,9H   4C,9H                                         Sugar beet  4C,9G       4C,8G   9C                                            Cotton      9C          4C,9G   4C,8G                                         PREEMERGENCE                                                                  Morningglory                                                                              3C,9G       8G      9G                                            Cocklebur   8H          8H      8H                                            Velvetleaf  9C          9C      2G                                            Nutsedge    9G          8G      5G                                            Crabgrass   5G          0       4G                                            Barnyardgrass                                                                             8G          3C,6G   2C,5G                                         Cheatgrass  4C,9H       9H      2C,7G                                         Wild Oats   4C,6G       2C,8G   4C,8G                                         Wheat       5G          5G      2C,8G                                         Corn        3C,8H       8G      3C,9H                                         Soybean     3C,6H       2C,4G   3C,4H                                         Rice        10E         4C,9H   10E                                           Sorghum     5C,9H       4C,8H   5C,9H                                         Sugar beet  10E         10C     5C,9G                                         Cotton      9G          8G      2C,8G                                         ______________________________________                                                  Cmpd. 42 Cmpd. 43  Cmpd. 44                                                                              Cmpd. 45                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            5C,9G    1C,3G     2C,7G   4C,8H                                    Cocklebur 3G       2C,8H     8G      2C,8G                                    Velvetleaf                                                                              4C,9G    2C,5G     4C,9H   4C,9G                                    Nutsedge  5G       5G        4C,9G   4C,9G                                    Crabgrass 3C,6G    0         3C,6G   2C,6G                                    Barnyardgrass                                                                           2H       2C,5H     3C,6H   5C,9H                                    Cheatgrass                                                                              5G       3C,9G     5C,9G   5C,9G                                    Wild Oats 5C,9G    3C,9G     7G      2C,8G                                    Wheat     8G       3G        2G      2G                                       Corn      10C      7H        3C,9G   4U,9G                                    Soybean   9C       3C,7H     9C      9C                                       Rice      9C       4C,9G     5C,9G   5C,9G                                    Sorghum   9C       4C,9H     9C      9C                                       Sugar beet                                                                              9C       4C,8G     9C      9C                                       Cotton    5C,9G    4C,7G     4C,8H   4C,9G                                    PREEMERGENCE                                                                  Morningglory                                                                            2C,9G    0         6G      5G                                       Cocklebur 4G       0         3H      8H                                       Velvetleaf                                                                              3G       3G        9C      9C                                       Nutsedge  0        0         4C,9G   10E                                      Crabgrass 2C       0         2C,5G   6G                                       Barnyardgrass                                                                           2C,6G    0         3C,8H   9H                                       Cheatgrass                                                                              3C,5GT   8G        9H      10E                                      Wild Oats 2C,7G    2C,6G     4C,8G   8G                                       Wheat     2C,7G    2G        4C,8G   8G                                       Corn      4C,9H    2G        4C,9G   2C,8G                                    Soybean   3C,5G    1H        3C,4H   3H,5G                                    Rice      10E      4C,6G     10E     9H                                       Sorghum   4C,9H    2C,3G     3C,9G   3C,9G                                    Sugar beet                                                                              10E      3C,6G     9C      10C                                      Cotton    3C,5G    2G        8G      4G                                       ______________________________________                                                  Cmpd. 46 Cmpd. 47  Cmpd. 48                                                                              Cmpd. 49                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            6G       5C,9G     2G      2G                                       Cocklebur 2C,9G    3G        0       4C,9G                                    Velvetleaf                                                                              0        3C,5G     3G      1H                                       Nutsedge  9G       0         0       2C,5G                                    Crabgrass 0        2G        0       0                                        Barnyardgrass                                                                           8H       7H        2H      3C,8H                                    Cheatgrass                                                                              5G       2C,8G     0       3G                                       Wild Oats 0        9G        0       0                                        Wheat     0        4G        0       2G                                       Corn      3H       4U,9C     2C,7H   7H                                       Soybean   2C,5G    9C        4C,9G   5C,9G                                    Rice      5G       4C,9G     8G      9C                                       Sorghum   3C,8H    4C,9H     6H      3C,8G                                    Sugar beet                                                                              2G       9C        4C,8G   3C,4H                                    Cotton    1H       4C,9H     2C,5G   3C,5H                                    PREEMERGENCE                                                                  Morningglory                                                                            3G       4H        0       7G                                       Cocklebur 2G       0         0       4G                                       Velvetleaf                                                                              5G       4C,9G     0       5G                                       Nutsedge  5G       0         0       3G                                       Crabgrass 2G       0         0       0                                        Barnyardgrass                                                                           3H       1H        0       0                                        Cheatgrass                                                                              8G       7H        0       3G                                       Wild Oats 0        4G        0       0                                        Wheat     0        2C,6G     0       0                                        Corn      5G       2C,6G     0       0                                        Soybean   0        2H        0       2C,3H                                    Rice      9H       2C,5G     0       8H                                       Sorghum   3C,8H    3C,5G     0       3C,6H                                    Sugar beet                                                                              7G       4C,9G     6G      3H                                       Cotton    0        6G        0       0                                        ______________________________________                                                  Cmpd. 50 Cmpd. 51  Cmpd. 52                                                                              Cmpd. 53                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            8G       6H        1C,2G   2C,5G                                    Cocklebur 5C,9G    10C       4C,9G   0                                        Velvetleaf                                                                              5C,9H    5C,9G     1C      3C,7G                                    Nutsedge  4C,9G    3C,9G     4G      0                                        Crabgrass 3G       5G        0       0                                        Barnyardgrass                                                                           6C,9H    9C        9H      3H                                       Cheatgrass                                                                              8G       3C,8G     0       0                                        Wild Oats 2C,5G    3G        0       0                                        Wheat     8G       3G        0       0                                        Corn      3U,9G    9C        6H      2C,9G                                    Soybean   9C       9C        3C,7G   4C,9G                                    Rice      6C,9G    9C        6G      8G                                       Sorghum   3U,9G    3U,9H     3C,8G   3G                                       Sugar beet                                                                              5C,9G    4C,9G     2C,3H   9C                                       Cotton    5C,9G    4C,9G     2C,4G   4C,9G                                    PREEMERGENCE                                                                  Morningglory                                                                            9G       9G        6G      2G                                       Cocklebur 9H       8H        7H      3H                                       Velvetleaf                                                                              9C       8G        5C,9G   3G                                       Nutsedge  9G       4C,9G     3G      0                                        Crabgrass 2C,6G    2G        0       0                                        Barnyardgrass                                                                           5C,9H    3C,9H     3C,7H   0                                        Cheatgrass                                                                              5C,9H    8G        5G      0                                        Wild Oats 2C,8G    3C,8G     0       0                                        Wheat     7G       3C,9H     0       0                                        Corn      3C,9H    3C,9H     4G      3G                                       Soybean   9H       3C,8H     3C,3H   2C,2H                                    Rice      10E      3C,9H     4C,8H   0                                        Sorghum   10E      5C,9H     3C,7H   2C,3H                                    Sugar beet                                                                              10C      9G        5G      3C,5G                                    Cotton    10C      9G        2G      3G                                       ______________________________________                                                Cmpd. 54                                                                             Cmpd. 55  Compound 56                                          Rate kg/ha                                                                              0.05     0.05      0.05    0.01                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        2C        4C,9G   3C,5G                                    Cocklebur 0        4C,5G     2C,9G   2C,7G                                    Velvetleaf                                                                              0        5C,8H     9C      4C,8H                                    Nutsedge  0        0         6G      2C,4G                                    Crabgrass 0        2G        2C,8G   2G                                       Barnyardgrass                                                                           0        3C,6H     4C,9H   2H                                       Cheatgrass                                                                              0        2C,5G     2C,9G   2C,8G                                    Wild Oats 0        0         2C,7G   0                                        Wheat     0        0         0       0                                        Corn      3G       1H        3C,7H   4H                                       Soybean   3C,4H    3C,4H     4CF,9G  5C,9G                                    Rice      2G       4C,6G     4C,9G   4C,9G                                    Sorghum   0        3C,4G     3C,9G   3C,6G                                    Sugar beet                                                                              1H       3C,4H     4C,8H   2C                                       Cotton    3C,4G    4C,7G     4C,9H   4C,8G                                    PREEMERGENCE                                                                  Morningglory                                                                            0        4G        9G      3G                                       Cocklebur 0        0         9H      3G                                       Velvetleaf                                                                              0        0         8G      3G                                       Nutsedge  0        0         0       0                                        Crabgrass 0        0         5G      4G                                       Barnyardgrass                                                                           0        0         7G      1C                                       Cheatgrass                                                                              0        0         3C,8G   5G                                       Wild Oats 0        0         9G      5G                                       Wheat     0        0         0       0                                        Corn      0        0         2C,8G   3G                                       Soybean   0        0         3C,7H   3C,4H                                    Rice      0        0         3C,8H   2G                                       Sorghum   0        0         3C,7G   2G                                       Sugar beet                                                                              0        5G        8G      6G                                       Cotton    0        0         6G      4G                                       ______________________________________                                                  Cmpd. 57 Cmpd. 58  Cmpd. 59                                                                              Cmpd. 60                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        5G        8G      0                                        Cocklebur 2G       7G        7G      0                                        Velvetleaf                                                                              0        2C,7G     3C,8H   0                                        Nutsedge  2C       3C,8G     5G      0                                        Crabgrass 0        0         7G      0                                        Barnyardgrass                                                                           0        3C,7H     3C,9H   0                                        Cheatgrass                                                                              8G       4C,9G     2C,9G   0                                        Wild Oats 2C,8G    3C,8G     3C,9G   2C,8G                                    Wheat     0        0         2G      0                                        Corn      2G       3C,9H     3C,9H   3C,9G                                    Soybean   1H       3C,9G     5C,9G   0                                        Rice      3G       2C,9G     5C,9G   8G                                       Sorghum   3C,7G    3C,9H     4C,9H   2C,7G                                    Sugar beet                                                                              2C,6G    5C,9G     5C,9G   0                                        Cotton    2G       2C,5G     4C,8H   0                                        PREEMERGENCE                                                                  Morningglory                                                                            0        3H        3C,6G   0                                        Cocklebur 0        5H        --      0                                        Velvetleaf                                                                              0        5G        5G      0                                        Nutsedge  0        5G        10E     0                                        Crabgrass 0        0         2G      0                                        Barnyardgrass                                                                           0        0         4G      0                                        Cheatgrass                                                                              0        2G        8G      0                                        Wild Oats 0        2C,5G     3C,8G   0                                        Wheat     0        0         2G      0                                        Corn      0        2C,5G     3C,6G   3G                                       Soybean   0        1C        2C      0                                        Rice      0        2C,5G     3C,8G   3G                                       Sorghum   0        2C,4G     3C,7G   2G                                       Sugar beet                                                                              0        3C,8G     3C,7G   0                                        Cotton    0        6G        4G      0                                        ______________________________________                                                  Cmpd. 61 Cmpd. 62  Cmpd. 63                                                                              Cmpd. 64                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        3G        2C,5G   9C                                       Cocklebur 0        2C,7G     9C      10C                                      Velvetleaf                                                                              0        0         4C,9G   9C                                       Nutsedge  0        9G        4C,9G   4C,9G                                    Crabgrass 0        0         0       4G                                       Barnyardgrass                                                                           0        2C,7H     1C,4H   4C,9H                                    Cheatgrass                                                                              0        4G        8G      9C                                       Wild Oats 0        0         10C     4C,8G                                    Wheat     0        0         5G      4G                                       Corn      0        2H        5G      5C,9G                                    Soybean 0 1H       4C,9G     4C,9G                                            Rice      3G       0         9C      9C                                       Sorghum   2G       3C,7H     4C,9H   4C,9H                                    Sugar beet                                                                              1H       2H        9C      9C                                       Cotton    0        0         4C,9H   4C,9G                                    PREEMERGENCE                                                                  Morningglory                                                                            0        0         1C      8H                                       Cocklebur 0        --        --      9H                                       Velevetleaf                                                                             0        0         0       9C                                       Nutsedge  0        0         0       3C,8G                                    Crabgrass 0        0         0       2C                                       Barnyardgrass                                                                           0        0         0       5C,9H                                    Cheatgrass                                                                              0        0         8G      10H                                      Wild Oats 0        0         2C,7H   5C,9G                                    Wheat     0        0         0       7G                                       Corn      0        0         5G      5C,9H                                    Soybean   0        0         1C      4C,8H                                    Rice      0        0         3C,8G   10E                                      Sorghum   0        0         3C,7G   10H                                      Sugar beet                                                                              0        0         8G      9G                                       Cotton    0        0         2G      9G                                       ______________________________________                                                  Cmpd. 65 Cmpd. 66  Cmpd. 67                                                                              Cmpd. 68                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            10C      5C,9G     3C,9H   4C,8G                                    Cocklebur 10C      4C,9H     3G      5C,9G                                    Velvetleaf                                                                              10C      3C,8G     4C,9G   2C,6G                                    Nutsedge  5C,9G    3C,7G     0       4C,9G                                    Crabgrass 7G       2C,5G     2G      0                                        Barnyardgrass                                                                           9C       9C        9C      3C,8H                                    Cheatgrass                                                                              9C       4C,9G     8G      5G                                       Wild Oats 10C      9C        9C      0                                        Wheat     4G       9G        9G      0                                        Corn      9C       10C       9C      4G                                       Soybean   5C,9G    5C,9G     5C,9G   3C,7G                                    Rice      9C       9C        9C      4C,9G                                    Sorghum   9C       9C        4C,9G   9H                                       Sugar beet                                                                              9C       9C        9C      3C,6G                                    Cotton    4C,9G    4C,9H     4C,9H   4C,9G                                    PREEMERGENCE                                                                  Morningglory                                                                            9G       10E       7H      7G                                       Cocklebur 9H       3G        6H      --                                       Velevetleaf                                                                             5C,9G    2C        1C      2G                                       Nutsedge  9G       3C,5G     0       8G                                       Crabgrass 4C,5G    2C        0       0                                        Barnyardgrass                                                                           9H       4C,8H     0       3C,8H                                    Cheatgrass                                                                              10H      8G        2G      2C,8G                                    Wild Oats 9G       9C        2C,4G   0                                        Wheat     9G       3C,9H     2C,5G   0                                        Corn      9G       4C,9G     3C,9G   5G                                       Soybean   9H       2C,4G     1C      1C                                       Rice      10E      9H        9H      9H                                       Sorghum   5C,9H    4C,9H     3C,8H   4C,9H                                    Sugar beet                                                                              9C       3C,8G     8G      8G                                       Cotton    8G       4G        3C,3H   6G                                       ______________________________________                                                  Cmpd. 69 Cmpd. 70  Cmpd. 71                                                                              Cmpd. 72                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        4C,9G     10C     5G                                       Cocklebur 2G       7H        7G      2G                                       Velvetleaf                                                                              2G       8G        4C,9G   0                                        Nutsedge  5G       3C,8G     4C,8G   2G                                       Crabgrass 0        2C,3G     3C,8H   0                                        Barnyardgrass                                                                           2H       3C,8H     5C,9H   0                                        Cheatgrass                                                                              3C,7G    2C,8G     8G      4G                                       Wild Oats 3C,7G    2C,3G     3C,5G   2C,8G                                    Wheat     0        0         3G      0                                        Corn      2C,3H    4C,9H     2C,9H   3C,9H                                    Soybean   3C,5G    4C,9H     9C      2C,8G                                    Rice      3C,7G    5C,9G     4C,9G   6G                                       Sorghum   3C,5G    3C,9H     4C,9H   3C,8H                                    Sugar beet                                                                              10C      10C       10C     3C,6G                                    Cotton    3C,7H    3C,9H     9H      0                                        POSTEMERGENCE                                                                 Morningglory                                                                            0        4G        8G      0                                        Cocklebur 0        0         7G      2G                                       Velvetleaf                                                                              0        4G        7G      0                                        Nutsedge  0        0         0       0                                        Crabgrass 0        4G        5G      0                                        Barnyardgrass                                                                           0        3C,7G     3C,8H   0                                        Cheatgrass                                                                              0        3C,8G     9H      0                                        Wild Oats 0        6G        2C,6G   0                                        Wheat     0        0         2G      0                                        Corn      0        3C,7G     3C,8G   0                                        Soybean   0        3C,7H     2C,7H   0                                        Rice      0        2C,8H     3C,9H   0                                        Sorghum   0        3C,7G     3C,8H   0                                        Sugar beet                                                                              5G       3C,9G     7G      0                                        Cotton    0        8G        8G      0                                        ______________________________________                                                  Cmpd. 73 Cmpd. 74  Cmpd. 75                                                                              Cmpd. 76                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            2C,8H    2C,5G     10C     10C                                      Cocklebur 2H       2C,6H     10C     9C                                       Velvetleaf                                                                              3C,8H    2C,5G     9C      9C                                       Nutsedge  0        0         2C,8G   2C,8G                                    Crabgrass 0        0         2G      0                                        Barnyardgrass                                                                           0        0         8H      3C,9H                                    Cheatgrass                                                                              0        0         3C,6G   8G                                       Wild Oats 0        0         3G      3C,5G                                    Wheat     0        0         2G      2C,5G                                    Corn      2C,6H    0         2C,9H   4C,9H                                    Soybean   2C,9G    2C,8H     2C,9G   9C                                       Rice      3G       7G        2C,9G   5C,9G                                    Sorghum   0        2C,5G     9H      4C,9H                                    Sugar beet                                                                              9C       1H        2C,5H   3C,8H                                    Cotton    3C,8H    7G        4C,9H   9C                                       PREEMERGENCE                                                                  Morningglory                                                                            0        0         8H      9H                                       Cocklebur 6G       0         9H      9H                                       Velvetleaf                                                                              5G       0         9C      10C                                      Nutsedge  0        0         5G      4C,9G                                    Crabgrass 0        0         0       3G                                       Barnyardgrass                                                                           0        2G        3C,9H   3C,5G                                    Cheatgrass                                                                              0        0         8G      9G                                       Wild Oats 0        0         3C,8H   8G                                       Wheat     0        0         6G      7G                                       Corn      3G       0         3C,9H   3C,9G                                    Soybean   2C,1H    0         3C,7H   8H                                       Rice      2C,3G    0         3C,9H   3C,9H                                    Sorghum   0        0         3C,8H   9C                                       Sugar beet                                                                              6G       5G        9G      7G                                       Cotton    0        0         2C,8H   7G                                       ______________________________________                                                  Cmpd. 77 Cmpd. 78  Cmpd. 79                                                                              Cmpd. 80                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            2C, 7G   9C        10C     3C, 7H                                   Cocklebur 10C      9C        9C      3C, 7H                                   Velvetleaf                                                                              2C, 8G   9C        9C      3C, 4G                                   Nutsedge  2G       5G        4G      0                                        Crabgrass 0        3G        0       0                                        Barnyardgrass                                                                           0        3C, 8H    7H      0                                        Cheatgrass                                                                              0        4G        0       0                                        Wild Oats 0        2G        0       0                                        Wheat     0        3G        0       0                                        Corn      2G       3C, 8H    3C, 9H  0                                        Soybean   3H, 7G   5C, 9G    5C, 9G  3C, 8H                                   Rice      7G       5C, 9G    5C, 9G  7G                                       Sorghum   5G       3C, 9H    4C, 9H  2C, 5G                                   Sugar beet                                                                              0        10C       9C      3C, 5G                                   Cotton    8G       4C, 9G    5C, 9G  3C, 6H                                   PREEMERGENCE                                                                  Morningglory                                                                            8G       9G        9G      0                                        Cocklebur 5G       --        9H      0                                        Velvetleaf                                                                              5G       8G        9C      0                                        Nutsedge  0        0         0       0                                        Crabgrass 0        0         0       0                                        Barnyardgrass                                                                           0        8H        0       0                                        Cheatgrass                                                                              0        3G        0       0                                        Wild Oats 0        2C, 5G    0       0                                        Wheat     0        0         0       0                                        Corn      0        2C, 7G    2C, 7G  0                                        Soybean   0        9H        3C, 8H  2C                                       Rice      5G       3C, 7G    2C, 8G  0                                        Sorghum   2G       10H       3C, 9H  3C                                       Sugar beet                                                                              8G       9C        4C, 9G  5G                                       Cotton    5G       4C, 8H    8G      0                                        ______________________________________                                                  Cmpd. 81 Cmpd. 82  Cmpd. 83                                                                              Cmpd. 84                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                            2C, 5G   5C, 9G    3C, 9H  3C, 8G                                   Cocklebur 3C, 4G   5C, 9G    10C     5C, 9G                                   Velvetleaf                                                                              3C, 3G   4C, 8H    10C     5G                                       Nutsedge  0        3C, 6G    5C, 9G  5G                                       Crabgrass 0        0         0       0                                        Barnyardgrass                                                                           2H       2C        3C, 9H  0                                        Cheatgrass                                                                              0        3G        2C, 5G  0                                        Wild Oats 0        0         2G      0                                        Wheat     0        0         3G      0                                        Corn      0        3C, 7H    9G      3G                                       Soybean   2C, 5G   4C, 8H    5C, 9G  2H, 5G                                   Rice      4G       5G        8G      5G                                       Sorghum   4G       2C, 4G    3C, 3H  4G                                       Sugar beet                                                                              2H       3C, 2H    3C, 8H  0                                        Cotton    2C, 3G   3G        5C, 9G  2G                                       POSTEMERGENCE                                                                 Morningglory                                                                            2C       7H        5G      3C, 3H                                   Cocklebur 3H       4C, 4H    9C      3C, 7H                                   Velvetleaf                                                                              9C       9C        9C      7G                                       Nutsedge  0        2C        5G      0                                        Crabgrass 0        2G        3G      0                                        Barnyardgrass                                                                           2G       3C        3C, 6G  0                                        Cheatgrass                                                                              2G       7G        8G      0                                        Wild Oats 0        2C, 5G    7G      0                                        Wheat     0        4G        5G      0                                        Corn      0        3C, 6H    2C, 8G  0                                        Soybean   0        3C, 4H    4C, 5H  0                                        Rice      2C, 3G   3C, 7H    2C, 7G  5G                                       Sorghum   0        3C, 7H    2C, 8G  2G                                       Sugar beet                                                                              9C       8H        8G      8G                                       Cotton    0        6G        5G      2C                                       ______________________________________                                                    Cmpd. 85     Cmpd. 86 Cmpd. 87                                    Rate kg/ha  0.05         0.05     0.05                                        ______________________________________                                        POSTEMERGENCE                                                                 Morningglory                                                                              4C,9G        4C,9H    3C,4H                                       Cocklebur   6C,9G        4C,9H    2C                                          Velvetleaf  4C,8H        4C,8H    0                                           Nutsedge    4G           3G       0                                           Crabgrass   4G           0        0                                           Barnyardgrass                                                                             3C,7H        3C,7H    0                                           Cheatgrass  0            2G       0                                           Wild Oats   3C,7G        0        0                                           Wheat       0            0        0                                           Corn        3C,7H        3C,6H    0                                           Soybean     5C,9G        5C,9G    2C,2H                                       Rice        4C,9G        2C,8G    2G                                          Sorghum     4C,9H        3C,9H    2C,3H                                       Sugar beet  5C,9G        9C       3C,5H                                       Cotton      4C,8H        3C,7H    1C                                          PREEMERGENCE                                                                  Morningglory                                                                              4C,8H        3C,5H    0                                           Cocklebur   8H           9H       0                                           Velvetleaf  10E          8G       4G                                          Nutsedge    7G           --       0                                           Crabgrass   1C           0        0                                           Barnyardgrass                                                                             3C,5G        2C       0                                           Cheatgrass  0            0        0                                           Wild Oats   2C,6G        0        0                                           Wheat       0            0        0                                           Corn        2C,5G        0        0                                           Soybean     3C,7G        3C,7G    3C,3G                                       Rice        3C,6H        3C,5G    0                                           Sorghum     3C,9H        3C,7H    3G                                          Sugar beet  4C,8G        9C       0                                           Cotton      6G           5G       0                                           ______________________________________                                                  Cmpd. 88 Cmpd. 89  Cmpd. 90                                                                              Cmpd. 91                                 Rate kg/ha                                                                              0.05     0.05      0.05    0.05                                     ______________________________________                                        POSTEMERGENCE                                                                  Morningglory                                                                           4C,8H    10C       5G      2C,7G                                    Cocklebur 3C,9G    9C        0       2H                                       Velvetleaf                                                                              3C,8G    10C       0       0                                        Nutsedge  3C,5G    2C,8G     0       0                                        Crabgrass 0        4G        0       0                                        Giant Foxtail                                                                           0        4C,9G     0       0                                        Barnyardgrass                                                                           0        9H        0       0                                        Cheatgrass                                                                              0        5C,9G     0       0                                        Wild Oats 0        2C,4G     0       0                                        Wheat     0        6G        0       0                                        Corn      0        3C,9H     0       0                                        Barley    0        7G        0       0                                        Soybean   4G       9C        1C,3G   2C,6G                                    Rice      7G       9C        0       0                                        Sorghum   8H       9C        0       0                                        Sugar beet                                                                              3C,7G    10C       0       3H                                       Cotton    3C,7G    10C       4G      8G                                       PREEMERGENCE                                                                  Morningglory                                                                            8G       9G        0       0                                        Cocklebur 7G       8H        0       0                                        Velvetleaf                                                                              5G       9G        0       0                                        Nutsedge  0        8G        0       0                                        Crabgrass 0        5G        0       0                                        Giant Foxtail                                                                           2C       9H        0       0                                        Barnyardgrass                                                                           0        8H        0       0                                        Cheatgrass                                                                              0        8G        0       0                                        Wild Oats 0        8G        0       0                                        Wheat     0        8G        0       0                                        Corn      0        9G        0       0                                        Barley    0        9G        0       0                                        Soybean   0        7H        0       0                                        Rice      4G       9H        0       0                                        Sorghum   2C,7G    5C,9G     0       0                                        Sugar beet                                                                              7G       9C        0       5G                                       Cotton    5G       8G        0       0                                        ______________________________________                                                         Cmpd. 92 Cmpd. 93                                            Rate kg/ha       0.05     0.05                                                ______________________________________                                        POSTEMERGENCE                                                                 Morningglory     0        2C,5G                                               Cocklebur        0        5C,9G                                               Velvetleaf       0        4C,9H                                               Nutsedge         0        2C,7G                                               Crabgrass        0        0                                                   Giant Foxtail    0        2C,6G                                               Barnyardgrass    0        9H                                                  Cheatgrass       0        2C,9G                                               Wild Oats        0        0                                                   Wheat            0        2G                                                  Corn             0        0                                                   Barley           0        0                                                   Soybean          3G       5C,9G                                               Rice             0        4C,9G                                               Sorghum          0        4C,9H                                               Sugar beet       0        4C,9G                                               Cotton           0        4C,8G                                               PREEMERGENCE                                                                  Morningglory     0        8G                                                  Cocklebur        0        7H                                                  Velvetleaf       0        5G                                                  Nutsedge         0        0                                                   Crabgrass        0        0                                                   Giant Foxtail    0        0                                                   Barnyardgrass    0        0                                                   Cheatgrass       0        0                                                   Wild Oats        0        0                                                   Wheat            0        0                                                   Corn             0        0                                                   Barley           0        2G                                                  Soybean          0        0                                                   Rice             0        4G                                                  Sorghum          0        4G                                                  Sugar beet       0        8G                                                  Cotton           0        5G                                                  ______________________________________                                    

The embodiments of the invention in which an exclusive property orprivilege is claimed are defined as follows:
 1. A compound of theformula ##STR32## and their agriculturally suitable salts, wherein: J is##STR33## W is O or S; R is H or CH₃ ;R₁ is H, C₁ to C₃ alkyl, C₁ to C₃haloalkyl, halogen, nitro, C₁ to C₃ alkoxy, SO₂ NR_(a) R_(b), C₁ to C₃alkylthio, C₁ to C₃ alkylsulfinyl, C₁ to C₃ alkylsulfonyl, CN, CO₂R_(c), C₁ to C₃ haloalkoxy, C₁ to C₃ haloalkylthio, C₂ to C₃alkoxyalkyl, C₂ to C₃ haloalkoxyalkyl, C₂ to C₃ alkylthioalkyl, C₂ to C₃haloalkylthioalkyl, C₂ to C₃ cyanoalkyl or NR_(d) R_(e) ; R_(a) is H, C₁to C₄ alkyl, C₂ to C₃ cyanoalkyl, methoxy or ethoxy; R_(b) is H, C₁ toC₄ alkyl or C₃ to C₄ alkenyl; or R_(a) and R_(b) can be taken togetheras --(CH₂)₃ --, --(CH₂)₄ --, --(CH₂)₅ -- or --CH₂ CH₂ OCH₂ CH₂ --; R_(c)is C₁ to C₄ alkyl, C₃ to C₄ alkenyl, C₃ to C₄ alkynyl, C₂ to C₄haloalkyl, C₂ to C₃ cyanoalkyl, C₅ to C₆ cycloalkyl, C₄ to C₇cycloalkylalkyl or C₂ to C₄ alkoxyalkyl; R_(d) and R_(e) areindependently H or C₁ to C₂ alkyl; R₂ is C₂ to C₆ haloalkenyl, C₃ to C₆cycloalkyl, C₃ to C₆ cycloalkyl optionally substituted with 1 or 2 CH₃groups, C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl, C₃ to C₆epoxyalkyl, C₂ to C₆ haloalkyl, CH₂ CH(OR₅)₂, ##STR34## phenyl which maybe optionally substituted with R₇, ##STR35## CH₂ C(O)CH₃, CN, OR₆, C₁ toC₆ alkyl substituted with OR₉, S(O)_(n) R₁₀ or NR₁₁ R₁₂, Q, CHR₈ Q orCH₂ CH₂ Q; R₃ is C₁ to C₆ alkyl, C₃ to C₆ alkenyl, C₃ to C₆ alkynyl, C₃to C₆ cycloalkyl which can be optionally substituted with 1 or 2 CH₃groups, C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl, C₁ to C₆haloalkyl, C₁ to C₅ alkoxy, C₃ to C₆ epoxyalkyl or C₁ to C₆ alkylsubstituted with OR₉, S(O)_(n) R₁₀, NR₁₁ R₁₂ or P(O)(OR₅)₂ ; R₄ is C₁ toC₃ alkyl substituted with 1-3 atoms of F, Cl or Br, C₃ to C₄ alkynyl,CH₂ CH(OR₅)₂, ##STR36## C₂ to C₆ haloalkenyl, C₃ to C₆ epoxyalkyl, CH₂C(O)CH₃, CN, C₁ to C₆ alkyl substituted with OR₉, S(O)_(n) R₁₀ or NR₁₁R₁₂, Q, CHR₈ Q or CH₂ CH₂ Q; R₃ and R₄ can be taken together with thesulfonamide nitrogen to form a saturated 5-or 6-membered ringsubstituted by one or more groups selected from L or a partiallysaturated 5- or 6-membered ring optionally substituted by one or moregroups selected from L; R₅ is C₁ to C₃ alkyl; R₆ is C₁ to C₅ alkyl; R₇is H, C₁ to C₃ alkyl, halogen, NO₂, CF₃, CN or C₁ to C₃ alkoxy; R₈ is Hor CH₃ ; R₉ is H, SO₂ R₅, C(O)R₅, CO₂ R₅, C(O)NR₁₁ R₁₂ or P(O)(OR₅)₂ ;R₁₀ is C₁ to C₃ alkyl; R₁₁ is H or C₁ to C₃ alkyl; R₁₂ is H or C₁ to C₃alkyl; m is 2 or 3; n is 0, 1 or 2; Q is a heterocycle selected from thegroup pyrrolidine, pyrrole, dithiolane, tetrahydrofuran, dioxane,thiazole, thiadiazole, pyrimidine and pyridine optionally substituted byone or more groups selected from L; L is C₁ to C₄ alkyl, C₁ to C₃haloalkyl, halogen, C₁ to C₃ alkoxy, C₁ to C₃ alkylthio, C₃ to C₄alkenyloxy, C₃ to C₄ alkenylthio, C₁ to C₂ haloalkoxy or C₁ to C₂haloalkylthio; A is ##STR37## X is H, C₁ to C₄ alkyl, C₁ to C₄ alkoxy,C₁ to C₄ haloalkoxy, C₁ to C₄ haloalkyl, C₁ to C₄ haloalkylthio, C₁ toC₄ alkylthio, C₂ to C₅ alkoxyalkyl, C₂ to C₅ alkoxyalkoxy, amino, C₁ toC₃ alkylamino or di(C₁ to C₃ alkyl)amino; Y is H, C₁ to C₄ alkyl, C₁ toC₄ alkoxy, C₁ to C₄ haloalkoxy, C₁ to C₄ haloalkylthio, C₁ to C₄alkylthio, C₂ to C₅ alkoxyalkyl, C₂ to C₅ alkoxyalkoxy, amino, C₁ to C₃alkylamino, di(C₁ to C₃ alkyl)amino, C₃ to C₄ alkenyloxy, C₃ to C₄alkynyloxy, C₂ to C₅ alkylthioalkyl, C₁ to C₄ haloalkyl, C₃ to C₅cycloalkyl, C₂ to C₄ alkynyl, C(O)R_(f), ##STR38## or N(OCH₃)CH₃ ; L₁and L₂ are independently O or S; R_(f) is H or CH₃ ; R_(g) and R_(h) areindependently C₁ to C₂ alkyl; Z is N; and X₂ is CH₃ or OCH₃ ;providedthat: (a) when A is A-1, then R₂ is other than CH₂ CF₃ ; (b) when R₃ orR₄ is CH₂ CF₃, then the other is CHF₂, CH₂ CH₂ F, CH₂ CH₂ Cl, CH₂ CH₂ Bror CH₂ CF₃ ; (c) when R₄ is CF₂ H, then R₃ is other than C₁ to C₃ alkyl;(d) when R₄ is C₃ to C₄ alkynyl, then R₃ is CHF₂, CH₂ CH₂ F, CH₂ CH₂ Cl,CH₂ CH₂ Br or C₃ to C₄ alkynyl; (e) neither X nor Y is OCF₂ H; and (f)when R₁ is H, then R₂ is other than OR₆.
 2. A compound according toclaim 1 wherein:W is O; J is J-1; and R₂ is C₂ to C₆ haloalkenyl, C₃ toC₆ cycloalkyl, C₃ to C₆ cycloalkyl optionally substituted with 1 or 2CH₃ groups, C₄ to C₇ cycloalkylalkyl, C₅ to C₆ cycloalkenyl, C₃ to C₆epoxyalkyl, C₂ to C₆ haloalkyl, CH₂ CH (OR₅)₂, OR₆, phenyl which can beoptionally substituted with R₇, ##STR39## CH₂ C(O)CH₃, CN or C₁ to C₆alkyl substituted with OR₉, S(O)_(n) R₁₀ or NR₁₁ R₁₂.
 3. A compoundaccording to claim 1 wherein:W is O; J is J-1; and R₂ is Q, CHR₈ Q orCH₂ CH₂ Q.
 4. A compound according to claim 1 wherein:W is O; and J isJ-2.
 5. A compound according to claim 2 wherein:R is H; R₁ is H, C₁ toC₂ alkyl, F, Cl, Br, NO₂, C₁ to C₂ alkoxy, C₁ to C₂ alkylthio, C₁ to C₂haloalkoxy, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN and is not para to thesulfonylurea bridge; A is A-1; X is CH₃, OCH₃, OCH₂ CH₃, OCH₂ CH₂ F,OCH₂ CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br; and Y is H, C₁ to C₃ alkyl,OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, SCF₂ H,cyclopropyl, C.tbd.CH, C.tbd.CCH₃ or CH(OCH₃)₂.
 6. A compound accordingto claim 3 wherein:R is H; R₁ is H, C₁ to C₂ alkyl, F, Cl, Br, NO₂, C₁to C₂ alkoxy, C₁ to C₂ alkylthio, C₁ to C₂ haloalkoxy, CH₂ OCH₃, CH₂SCH₃ or CH₂ CN and is not para to the sulfonylurea bridge; A is A-1; Xis CH₃, OCH₃, OCH₂ CH₃, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CF₃, CH₂Cl or CH₂ Br; and Y is H, C₁ to C₃ alkyl, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃,N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, SCF₂ H, cyclopropyl, C.tbd.CH, C.tbd.CCH₃or CH(OCH₃)₂.
 7. A compound according to claim 4 wherein:R is H; R₁ isH, C₁ to C₂ alkyl, F, Cl, Br, NO₂, C₁ to C₂ alkoxy, C₁ to C₂ alkylthio,C₁ to C₂ haloalkoxy, CH₂ OCH₃, CH₂ SCH₃ or CH₂ CN and is not para to thesulfonylurea bridge; A is A-1; X is CH₃, OCH₃, OCH₂ CH₃, CH₂ F, OCH₂ CH₂F, OCH₂ CHF₂, OCH₂ CF₃, CF₃, CH₂ Cl or CH₂ Br; and Y is H, C₁ to C₃alkyl, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃,OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ SCH₃, SCF₂H, cyclopropyl, C.tbd.CH, C.tbd.CCH₃ or CH(OCH₃)₂.
 8. A compoundaccording to claim 5 wherein:R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂CN; R₂ is C₃ to C₆ cycloalkyl, C₂ to C₄ haloalkenyl, CH₂ CH₂ F, CH₂ CH₂Cl or CH₂ CH₂ Br; X is CH₃, OCH₃, OCH₂ CH₃, or OCH₂ CF₃ ; and Y is CH₃,OCH₃, CH₂ CH₃, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 9. A compound according toclaim 6 wherein:R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂ CN; R₂ is Qor CH₂ Q; X is CH₃, OCH₃, OCH₂ CH₃, or OCH₂ CF₃ ; and Y is CH₃, OCH₃,CH₂ CH₃, CH₂ OCH₃, NHCH₃ or CH(OCH₃)₂.
 10. A compound according to claim7 wherein:R₁ is H, Cl, OCH₃, OCF₂ H, CH₂ OCH₃ or CH₂ CN; R₃ is C₁ to C₃alkyl, C₃ to C₄ alkenyl, C₃ to C₄ alkynyl, C₃ to C₆ cycloalkyl or C₁ toC₂ haloalkyl; R₄ is C₂ to C₄ haloalkenyl or C₃ to C₄ epoxyalkyl; X isCH₃, OCH₃, OCH₂ CH₃, or OCH₂ CF₃ ; and Y is CH₃, OCH₃, CH₂ CH₃, CH₂OCH₃, NHCH₃ or CH(OCH₃)₂.
 11. The compound of claim 1 that isN-cyclopropyl-N'-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide.12. A composition for the control of undesired vegetation consistingessentially of a compound of claim 1 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 13. A composition forthe control of undesired vegetation consisting essentially of a compoundof claim 2 and at least one of (a) a surface active agent, and (b) asolid or liquid diluent.
 14. A composition for the control of undesiredvegetation consisting essentially of a compound of claim 3 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.15. A composition for the control of undesired vegetation consistingessentially of a compound of claim 4 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 16. A composition forthe control of undesired vegetation consisting essentially of a compoundof claim 5 and at least one of (a) a surface active agent, and (b) asolid or liquid diluent.
 17. A composition for the control of undesiredvegetation consisting essentially of a compound of claim 6 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.18. A composition for the control of undesired vegetation consistingessentially of a compound of claim 7 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 19. A composition forthe control of undesired vegetation consisting essentially of a compoundof claim 8 and at least one of (a) a surface active agent, and (b) asolid or liquid diluent.
 20. A composition for the control of undesiredvegetation consisting essentially of a compound of claim 9 and at leastone of (a) a surface active agent, and (b) a solid or liquid diluent.21. A composition for the control of undesired vegetation consistingessentially of a compound of claim 10 and at least one of (a) a surfaceactive agent, and (b) a solid or liquid diluent.
 22. A composition forthe control of undesired vegetation consisting essentially of thecompound of claim 11 and at least one of (a) a surface active agent, and(b) a solid or liquid diluent.
 23. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 1.24. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 2. 25. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 3.26. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 4. 27. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 5.28. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 6. 29. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 7.30. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 8. 31. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of a compound of claim 9.32. A method for the control of undesirable vegetation comprisingapplying to the locus of such vegetation an herbicidally effectiveamount of a compound of claim
 10. 33. A method for the control ofundesirable vegetation comprising applying to the locus of suchvegetation an herbicidally effective amount of the compound of claim 11.